Issei: The (secret) Playboy Lucifer
by YagamiNguyen
Summary: Smut with plot. In this story Issei, formerly Issei Gremory (and Hyoudou) is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one know about it, right? Issei/Harem. Warning: Hardcore and Incest.
1. The Soon to be Harem King

**ShoKazuma allowed me to adopt this story of him, so hope you don't mind me spread my lemon coverage range to High School DxD as well. Omni-Creator Kami of Anime asked me if I could adopt this story a pretty long time ago, so yeah after some deep thought I had decided to adopt it. Cannot let a master piece like this get dropped, can't I**

 **Since I have a hand in the making of this story, I know the direction this story is going to lead, so hopefully you will enjoy it now that it in my hand.**

 **I put two chapters of his together and added something he didn't add into this story in the first place: The lemon scene between Issei, Sera (Serafall's mother) and Raven (Ravel's mother)**

 _ **I will change this to somewhat porn with plot and some crossover to make it interesting.**_

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 **Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one know about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

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 ** _Issei: The Playboy (secret) Lucifer_**

 _ **Chapter 1**_

 _ **The soon to be Harem King**_

Issei Lucifer yawned loudly in boredom as he sat inside his office with multi batches of paperwork standing on his table. He had faced many enemies, stopped many threats that threatened his people and had been the Maou Lucifer for nearly one hundred and fifty years, but paperwork was always his greatest enemy.

He loved his job but Issei didn't sign up for this.

Lucifer was just a title, he was formerly known as Issei Gremory, the first son of Lord Gremory and Venelana Gremory. Unlike the other descendants of Gremory, who had beautiful crimson hair and blue-green eyes, Issei inherited the Bael's brown hair and brown eyes from his mother. He was tall, standing at the fifteen of five foot nine and his frame was lean, but muscular and well toned. Even though he was more than two hundred years old, due to her devil lineage, he had the appearance of a youthful man in his early 20's.

It was just a normal day at work for the Lucifer of the Underworld.

In one way or another, it's a normal day… as normal as it could until you know about what was happening underneath his table.

Sitting underneath the desk between Issei's spread thighs was a beautiful maid with black hair and voluptuous frame, her mouth stretched wide as she gently sucked upon the massive fifteen inch erection Issei called his dick. She was called in for some mundane reason, as soon as she had closed the door to his office, Issei allowed her perform the duty every maid within his house, the Lucifer Mansion had to do every time he called one of them in, in private. She freed his dick from its confines, and proceeded to try and suck his nuts off through his pole. She had been at it for over half an hour.

He might be a kind and caring leader whom everyone love and greatly respect, but in truth, one could call him a playboy or Casanova with the amount of woman he slept with nearly every day. A busy life of a Maou, time like this, could be extremely stressful so sex was the only way for him to reveal that stress and relax his mind as well as body.

Aka, his great libido.

"Ah~, that's it… just like that." Issei moaned in satisfaction as the maid grabbed a hold of his hips to keep him in place and kept his prick completely encased in her throat before she proceeded to swallow upon it as hard and fast as she could. Not many could deepthroat him like this, it always blew Issei's mind whenever his women do it willingly.

But still, this maid wasn't as good as a certain maid he knew and loved more than anyone else.

Unfortunately, she wasn't the best person he wanted to be the one who would catch him in this situation.

"Ise-sama, here are the files you need to sign." Speak of the she-devil and she would definitely appear. A beautiful and incredible voluptuous woman appearing to be in her early twenties, with silver hair and matching eyes stepped into the room carrying a whole new batch of paperwork in her hand stepped into the room. Her hair, which flowed all the way down to her back, featuring a long braid on each side with small blue bows at the ends, while the rest was let down, ending in twin braids. She was wearing a blue and white French maid outfit with long sleeves and a white maid headband over her head, with red lipstick as a cosmetic accessory.

"Oh hey, Grayfia!" Issei greeted her with a nervous smile, unconsciously pushed himself and the maid who was sucking him further underneath the table. This woman was Grayfia Lucifuge, she was his Queen, known as the Strongest Queen of the Underworld and the Silver-Haired Queen of Annihilation. She was a girl who came from the Original Household of Lucifer, who dedicated their life to serve the Maou Lucifer of the Underworld. Which explained why such a beautiful, attractive and powerful like her became his personal maid.

Unfortunately or fortunately enough, depend on the situation, she was also his wife.

"These are reports and requests from the House of Glasya-Labolas," Grayfia said and put the batch down his table. Issei could only nod his head and tried to act as normal as possible "I recommend you read them carefully before signing them." She then noticed the uncomfortable expression on his face, but she could also spot something strange from him as well "Are you okay?"

"Of course, why you ask?" He asked. The maid clearly didn't know what was happening and kept on deepthroating his cock like a pro. Issei was also very close to cumming so he was in an extremely tight situation currently. "I'm…Ah~… fine of course." He spilled it.

Grayfia looked at him for a second before turning her eyes to his table then back at him. It didn't take her long to realize it.

"Ise-sama!" She raised her voice, nearly yelled as she abruptly approached him and pushed Issei roughly backward, forcefully removing his cock from the mouth of the maid underneath the table, making it swing around wildly. To say Grayfia was angry was a huge understatement, but she wasn't feeling surprise, because this wasn't the first time she found him in situations even worse than this in the past two weeks.

"Grayfia-sama!" The maid was shock and very terrified to find the strongest Queen glaring murderously at her master.

"I can explain…" Issei held his hands out defensively, trying his best not to freak out. But it wasn't very convincing when his cock and balls were pretty much visible "please, it's not what it looks like."

"Ise-sama!" Grayfia gritted her teeth in anger and raised her fist "How many times do I have to tell you that you're not allowed to commit adultery? You're a Maou, please remember that!" She reminded him, but her fist was also shaking. He knew what was going to come next.

He was punched squarely in the face with so much force that he thought she just cracked his skull him.

 _Line Break_

"Please Grayfia let me explain!" Issei begged while following behind Grayfia at the two of them entered her room. It was clear to him that his wife was still extremely furious at him.

"There is nothing to explain Ise-sama." Grayfia said emotionlessly and grabbed a bottle of wine and a cup "You clearly don't know to keep it in your pant." She poured the wine into the cup until it was full and gulped it down her throat in one gulp. She then poured herself another one "Have you ever considering what will happen if someone find out about you having that kind of relationship with your servants? How many time I have to remind you that you're not allowed to have a harem in anyway?" she gulped down another cup full of wine and was about to take another one but Issei grab it from her hand and put it to the side.

"Hey, don't drink that much. We both know you has low alcohol tolerance." He said and Grayfia glared at him "and what you're drinking is Soda, not wine." Grayfia turned back to look at the bottle in her hand and growled in annoyance. This made Issei chuckle but he had to quickly move his head to the side to dodge another incoming punch. Grayfia then put the bottle away and turned around.

"Now if you excuse me, Ise-sama I have works to do and a maid to fire" As soon as she took the first, Issei grabbed her hand and swung her around into his chest, his hand put on her ass and grope it "What do you think you're doing?" she glared at him and asked with a cold tone.

"Showing you that you're still my favorite and beloved wife." Issei smirked and squeezed harder, feeling her round ass through the thin fabric of her dress.

"I'm currently on duty, Ise-sama." Her eyes didn't get any less murderous, but her tone soften a little. He ignored her statement and put his other hand onto her breast, stimulatingly groping her ass and tit at the same time. A smirk appeared on his face when Grayfia let out a soft moan.

He just know the way to turn her on.

His hand suddenly left her breast and placed around her neck, putting a little force into it and surprising Grayfia.

"Do you know how much frustration a man can get if he got cock-blocked? Especially when he was about to cum?" Issei asked "Do you know why I like those maids so much? Because they know how to perform their duty in pleasing my master. My personal maid, also my own wife however, don't really know how and the only time we can spend our time together is at weekend, her days off."

"What do you want me to do, Ise-sama?" she asked, her face spread out and a smile appear on his face. While she was furious at her husband for cheating on her so many times like that, she still loved him dearly and had the pride of a woman, the pride of a wife. When she could do nothing to change the way he was, she could only show him that she was the best, so he would never look at any women other than her.

"You won't leave this room until I'm satisfied." Issei smirked and took the both of them to her bed before turning her around, grinding his cock against her ass. Both of his hands fondled and played with her large breasts "We're going to have so much fun Grayfia!" he kissed her cheek, planting kisses along her long neck before tearing her shirt away.

His hand glowed with the aura of crimson and he moved it on her blue and white attire. With the power of destruction, her maid uniform vaporized into nothingness and he kept doing it until she was in nothing but her garter belt, white stockings and silver thong. He returned his hand to her large, bared tits after deactivating his power. They were firm, and extremely soft as well.

"Of course" Grayfia muttered, standing still so her King could play with her tits the way he want, though he couldn't stop moaning when he flicked her nipples with his fingers "Your favorite?" She knew that he loved breasts more than anything else on a woman's body.

"My favorite." Issei admitted and smashed her tits together, rubbing them against each other fast before roughly pulling them apart. Issei then turned her around and pushed her down to the bed, his tits bouncing because of such action "Time for some serious action Grayfia." He smirked and stepped forward until he was standing in front of her.

"Yes, Issei-sama" The maid nodded her head submissively then reached her hand out to unbuckled his belt and pulled down his pant, freeing his semi-hard member.

Putting one hand on his thigh and the other around his cock, Grayfia started slowly stroking him, but she couldn't resist the tempting sight for long after all this time. The Queen opened her mouth and gave his a long wet lick from the balls to tip of his cock. Then, she started licking his cock like a child licking her lollipop, stimulatingly moving her hands on his length. It didn't take her long to get him fully erect, standing proudly at the length of fifteen inches and as hard as steel.

Issei put his hand on Grayfia's head and moaned in pleasure when Grayfia stopped her licking and her full lips suddenly enveloped the head of his penis, making a gasp of bliss rushed through him.

His Queen sucked on his cock like a baby on a nipple, relishing the taste and texture. She tickled his dick hole with her nimble tongue and gently caressed the rim of his glans with her ruby red lips. She teased him for a blissful while before releasing his penis with a wet smacking noise.

"Get ready Ise-sama because your Queen is about to do her duty." she giggled and got on her knees. Grayfia pursed her lips and let a large blob drool pour down on the fifteen inches meat pole. With loving care she massaged the pulsating shaft until it was coated in a thick layer of glistening slime and beads of it were running down over his balls. She blew him a kiss before shoving the massive dick into her mouth once again.

Her head bobbed back and forth along the greased shaft, accompanied by muffled moans of pleasure, while her abounding tits bounced in the rhythm. The luscious woman could feel his hard erection slide over her supple tongue and squeeze deeper past her gums. She could immediately recognize the familiar manly taste of the hard cock inside her, she could even feel the veins below its skin pulsating.

Her pussy was burning with desire, but like always, her master's need go first. After wetting her white thong, a bead of warm juices trickled down her inner thigh and sent a shiver down her spine.

The young man started answering her movements and thrust his pelvis towards her, sending a tremble through the book shelf every time. He grunted with every thrust that shoved his penis a little bit further down his Queen's throat. From time to time, she would let Issei's cock slip out and indulge in a profound lick of his shaft and balls. She nibbled on its head and massaged the crest with swift fingers, only to then shove it back into the hot wetness of her avid mouth.

Finally she felt his cock slip past her uvula and all the way down her throat, the power of the man's thrust shoving it inside until her wet lips kissed his pelvis. Gently she pulled her head back and let the formidable cock slip out of her mouth. Thick strands of drool remained and stretched from the glans to her glistening lips.

She repeated the process again and again before starting sucking his pole with burning passion. Issei at this time had grasped her hair again and move his hip slightly to meet with her. Her tits huge were jumping up and down with every thrust, a sight that aroused him even further.

"Yes! Yes yes! Almost there!" He moaned through his teeth. Grayia moaned, hungry for his cum "Man! You're the best Grayfia."

Finally felt the ecstatic waves of his orgasm well through his long shaft and unloading pulse after pulse of thick, hot cum into Grayfia's insatiable mouth. She swallowed every drop of it with lustful eagerness. Eventually she let the heaving organ pop out of her mouth and started to lick it clean. A few belated spurts ended up on her face and on her sweaty tits. Grayfia kept stroking the relaxing shaft, to make sure she got every last dribble out of it. She breathed a sigh of happiness as she wiped the semen of her soft skin to lick it up.

"Man that was awesome, Grayfia!" Issei sighed in satisfaction and looked at Grayfia, who was wiping the cream on her face and put them into her mouth.

"Your cum is very delicious Issei-sama" the silver haired Queen smiled "Thank you."

"How about another treat?" Issei asked and Grayfia's eyes shone with excitement, but immediately found herself moaning when he reached his hands down to pull her breasts toward him by her nipples "How about in the form of a hotdog?" Issei asked slyly, and Grayfia immediately knew what he wanted.

"You really love breasts, don't you?" Grayfia asked with a small smile

"Of course, especially when they are wrapped around my cock."

Using both hands, she wrapped her soft melons around his dick and squeezed them together. The sensation was overwhelming. Issei had to lean back and close his eyes for a second to control himself. When he looked back down, his Queen already worked his cock, moving her breasts up and down on his dick and licking the tip of his cock every time it came up through her incredible cleavage.

She was smiling and giggling, so happy as she got him moan with her big tits. Issei was happy too. It didn't take long for him to explode. The first rope of his cum hit her chin and neck, the second hit the tops of her tits, which were heaving up and down with her breaths. She started to rub it all in, driving him crazy.

"Open your mouth" Issei said and gently pulled Grayfia's head back with one hand and the other stroking his cock, positioning it above her lips. Grayfia did what she was told and immediately got her mouth full of his cream. The two stayed like that for several seconds before Issei's orgasm finally died down. Grayfia savored it with her mouth before gulping it down her throat, opening her mouth again to show him there was nothing left "I think I will have a taste, hope you don't mind." Issei said and grabbed the waistband of her thong, smashing her legs together and pulling the small undergarment off her body, revealing her soaking wet cunt.

Issei then kneeled down until her pussy was right in front of his face, his arms wrapped around her thighs. Issei then slid one finger into her cunt, gently crawling the inside of her vagina. Her pussy was wet, soft and of course really hot. He couldn't wait to have his cock inside.

"Please, enjoy yourself, Ise-sama." Grayfia moaned out and leaned back, supporting herself with her elbows, thrusting her hip slightly against his finger to get herself some more pleasure. With a smirk, Issei pulled his finger out and leaned down to touch her cunt with his tongue, loving the taste of her juice.

He then planted several kisses on her beautiful pussy before driving his tongue into her pussy again, this time he tried to reach as far as possible into her, making Grayfia moan out in delight. More juices produced from her pussy and Issei drank them eagerly, just like how Grayfia drank his cum. Issei then put more effort into eating her pussy, using his mouth and lips to drive her with pleasure.

"Oh! Don't stop, don't stop, don't stop! Please don't stop!" Grayfia moaned out and cried in pleasure as he ate her, his tongue stroked flicks on her clit "Oh fuck. I'm cumming. Now. Now, Oh fuck, fuck, fuck, fuck. Fuuuuuuck!" Her juice splashed against his face and there were no chance for him to gulp it all down. Issei waited a few second for Grayfia to get out of her high and climbed on the bed to place his lips against hers, letting the woman taste her own juice.

"You're so amazing, Ise-sama" Grayfia moaned out

"And you sure know how to cum, Grayfia." Issei kissed his lips down to her neck, occupying his hand with her large breast "What a dirty Queen!" he kissed her one last time before removing himself from her. Issei moved to the head of the bed and laid his back down on the pillow, his cock pointing upward and legs spread slightly "It's time for you to return to your duty of pleasuring your husband."

"Hai!" Grayfia nodded her head submissively and crawled to Issei, straddling his erect member, Grayfia took his cock into her hand and positioned the tip at her pussy entrance before slowly sinking herself down, moaning quietly as his cock pierced her for the first time in a week. Issei put his hand on her thighs and guided her down until her ass met his lap, his cock buried inside her cunt.

"Let me rock your world, Ise-sama" Grayfia smiled sexily and put her hands at the back of her head, starting to rock her body on his cock with a steady pace. This pose allowed her tits to bounce freely, sometime slapped against her chin but she knew he loved it, because while moaning his eyes were gluing to the bouncing orbs, plus it also turned her on just by having him looking at her like that.

For several minutes, Issei just laid there and let Grayfia jumped his boner. She was rocking his world for sure, her ass slapped against his thighs every time she let herself fall down, but her strong legs managed to lift herself up right after that. She kept herself in that posture, allowing her tits to bounce wildly, turning him on with the sexy sight.

But he wasn't someone who would lay down and do nothing, even if it felt really good so Issei decided to take action once again, grabbing Grayfia's hip and rolling the both of them around with him on top. When they were in the place he wanted, Issei pulled his hip back until the bulbous head of his cock still remaining inside before slamming it back down, sliding his member into her fold once again. He fucked her slow at first before catching a nice rhyme, bringing both of them an unthinkable amount of pleasure.

Grayfia was trying not to outright scream out from pleasure but the force and angle of Issei's thrusts were driving her insane. Issei didn't seem like he was going to let up on her either. She felt her master's hands leave her ass but barely a second later she felt him grab a hold of her tits before he put his face into her cleavage, taking as much of her flesh into his mouth as possible before his target changed to her nipple.

Almost out of nowhere a huge orgasm ripped right through Grayfia, her body went rigid as she came her brains out around his cock, becoming even tighter for him.

"Shit, Grayfia, you're so tight!" Issei groaned out and tried his best to keep his hip moving, feeling his orgasm approaching "I'm about to cum, where do you want it?"

"Inside! I want you to cum inside me!" Grayfia cried out and wrapped her legs around his waist, preventing him from pulling out. He was about to reason with her, but Issei couldn't hold back any longer. Thrusting up into Grayfia the powerful Maou unleashed a huge dose of spunk deep into her womb. He stayed like that for several seconds, lying flat on Grayfia's front body and could only move his hip slightly to bring out more cum in his scrotum. As Issei finished cumming he pulled his slightly softening cock out of Grayfia's pussy and a huge wave of thick white goo followed his withdrawal.

"That was, absolutely amazing." Issei grinned. Issei could only consider what just happened his best sexual experience ever "I think I was just being reminded why I love you the most Grayfia."

"I am glad that you like it, Ise-sama." Grayfia managed to push herself to her knees behind him, pressing her breasts against his back and started placing soft and loving kisses on his jaw and neck. Issei's grin widened when he felt her hands on his cock again. "Please Ise-sama, promise me that you will never sleep with any women other than your wife again." She gave him her best puppy dog eyes, something that he could never refuse.

For an extremely beautiful woman, she sure knew how to use it to look cute.

"I will, but no promise." Grayfia forcefully squeezed his balls "Oh right oh right, I won't."

Grayfia grinned slyly and removed herself from her husband's body and pushed herself back "What would you like to try next, Ise-sama?"

"On your hands and knees, I would like to fuck your ass." Grayfia happily obeyed his order and got on her hands and knees, bending her back to stick her ass out as high as possible, shaking them invitingly. Issei immediately got behind her and placed both of his hands on her supple ass cheeks.

Her ass felt so good in his hands that he couldn't stop himself from giving her a hard spank.

"Kya~, Ise-sama."

"Sorry, can't help it" Issei chuckled and spread her ass cheeks apart, putting his cock into her ass crack and squeezed them back together, slightly thrusting his hip "Your ass is as incredible as you're, Grayfia."

"Then please, have your way with them." She smiled and braced herself "I'm ready."

"Gladly, my dear." Putting one hand on her hip, Issei lined his cock with her rosebud and slowly pushed himself in, moaning out loudly at the incredible tightness. Her anal crushed his cock with great pressure, like a gloves several size too small to his dick. When he was sheathed inside her, Issei had to put it like that for a few seconds to get use to the tightness.

"W-what? Too tight for you, Ise-sama?" Grayfia asked teasingly with one eyes closed. The woman groaned out slightly in pleasure when Issei slid one inch of his dick in and out of her anus, letting her get used to his size again "You're so big inside me, Ise-sama" " she sighed as he slowly fucked his cock into her butt.

Issei then sped up, shoving his big, thick meat up his Queen's butt, his hands left her hip and took a hold of her arms, Issei pulled them back by the elbow, causing her back to arch even more than before and her breasts to jut out and bounce. He pulled his hips back before slamming forward into the now moaning women's anus, setting an immediate and fast pace as he started fucking her in the ass. The fucking Issei gave her caused her boobs to bounce up and down rapidly striking her chin.

However, he was close to cumming faster than he expected, so Issei had no chance other than increasing his speed to savor this moment longer. He put every ounce of his muscle into work. Taking his speed to a whole new level, Issei's hips were a blur as his pelvis met Grayfia's ass. Swiftly moving his hands up to her chest he grabbed onto her wildly bouncing tits and used them to pull the screaming women flush against his body. Kissing her neck and keeping up his pace the fucked stupid look on her face seemed to become even more dopey now that he had picked up the pace even further.

"SHIT! Cumming!"

"ISSEI!" Grayfia screamed out when once again her husband flooded her inside with his cum. Think and hot sperm flowed into her systems and painted everything white. Her eyes rolled into the back of her head as she then experience a mega-orgasm. Her body twitched around and almost like a vibration for his dick, milking more of his come out of her fold.

It didn't help that her husband was as hung as a dragon and could come just as much.

"Oh man! I feel like I'm the luckiest man in the world right now" Issei groaned out when he slowly pulled his cock out of his wife's asshole, but suddenly thrust it back into her through her pussy, shocking his maid at the sudden penetration "you of all people should know that we're far from done Grayfia." He kissed the side of her hip and started to recklessly move his hip again.

This was why she limit their sex life to weekend only.

 _Line Break_

It was midnight and for the first time, the Queen's chamber finally fell into silence.

A very satisfied Issei laid on the his wife's bed with her sleeping soundly at his side, with her arms wrapped around his chest and head rested on his strong arm. It was definitely one of the best sexuality experiences between the two of them ever since they had been together and he had enjoyed every single moment of it, just like his wife even though her pride would never let her voice it out loud.

"Ise…" he heard Grayfia muttered in her sleep and unconsciously snuggled closer into his body. A stupid smile appeared on his face because he could feel her breasts pressed tightly against his body, too bad that he could touch them but having them like this was just as good.

[ **Enjoying yourself, partner?** ]

A voice then suddenly called out to him and Issei raised his left arm up to see his palm glowing the color of green.

"Yo Ddraig, been wondering why you're so quiet lately" Issei spoke up, earning a light chuckle from the dragon within him.

[ **With how your life turned out, it will be better if I don't disturb you, partner. Plus, you seem like you're greatly enjoying the silver haired Queen's company.** ]

Two weeks had passed since his death.

Two weeks had passed since the world reset.

Two weeks had passed since he found out in this world, he had replaced Sirzechs Gremory's very existence and become Maou Lucifer, the first son of Lord and Lady Gremory, the hero of the Great War and husband of Grayfia Lucifuge, sharing the same romantic love story the Grayfia of his old world shared with her husband, Sirzechs.

Not to mention two weeks had passed since he found out about the awaken of his dragon libido, triggered by the enormous amount of demonic energy he carried within him.

His life took a massive U-turn two weeks ago, in a way he would never expect.

All of this was an effort of Ophis and Great Red in saving his life after he was killed by Balba Beelzebub and the Samael Curse. His very soul was damaged to the point even the two most powerful beings couldn't help Issei. In order to save him, they had no other way than reset the entire world from the begin of time. Ophis and Great Red combined their power and created a whole new universe, in which he was everything he mentioned above, and placed what was left of his soul, his memories and consciousness into Issei Lucifer's soul.

Other than his existence replaced Sirzechs Lucifer, the rest flowed normally.

He was shocked at first, but with Ddraig's guidance he managed to settle everything into place. Things was no longer the same around with him being the Maou and carrying the memories of how the future was going to turn out. Not to mention that the love of his life, Rias Gremory was now his biological sister and was going to be born in the next two weeks.

Being a Great Maou, no problem. Being a kind and caring leader, no problem too thank to the memories of the original Issei Lucifer.

However, his dream of having a harem for himself was severely threatened because of his status.

"Can't believe that Grayfia-san is the woman I lost my virginity to." Issei sighed before smiling. It was strange, in many way. It was clear that he wasn't the one who took Grayfia's virginity, but his first time was in his memories and he could remember all of it very clearly "I thought it's going to be Rias, or Akeno-san or Asia…"

[ **Relax partner, with the way you're now, I believe you're going to have your chance in the future, Lucifer-sama.** ] the soul of the legendary heavenly dragon joked [ **Oh please remember that you have a wife.** ]

"Hey, it can't be help that I have an dragon-like libido" Issei groaned, even right now he was feeling rather horny. He was Issei Lucifer, the strongest devil with unrivalled demonic energy, which unfortunately had triggered his dragon like physique to the whole new level. Ddraig let him know that the stronger the dragon, the hornier they become.

It in their primal instinct, fighting and fucking, the stronger got everything to themselves even the female.

And now he shared the same thing, combine with the stress of his daily life at work, it became unbearable. Grayfia wasn't the most outgoing woman in their sex life, as she normally put her duty at his maid before him so he had to ask the maids around his residence for help. The girls were more than happy to please their master and Issei felt like he just archived greatest fantasy after fucking the first maid.

He was very thankful that Issei Lucifer's personalities and tastes were very similar to him, also had a reputation of secretly cheating on his wife with lot of women before or else it was going to be very awkward to the girls he slept with.

[ **Get some sleep partner, because I have the feeling that tomorrow is going to be yet another day you have to work your ass off to keep your reputation as the leader of a whole Faction,** ] Ddraig wisely advised [ **as well as to satisfy your own libido or else you will lost your control**.]

"I know, good night Ddraig." Issei smiled before closing his eyes.

[ **Good night partner** ]

 _Line Break_

Grayfia Lucifuge was walking to her husband/master's office rather numbly. What happened last night was simply incredible, even if she would never admit out loud and of course, never to Issei. Devils were famous for the prowess if sexual activities, but what her husband did last night was way off the chart. Grayfia knew that he was good and definitely knew how to use his larger than normal asset, but in the past two weeks he had been with more women than she could count in a month and all of them admitted that they were fucked like never before and said he was the greatest man they had ever been with.

She had been wondering why she hadn't dropped such an unfaithful husband before, but found herself loved him too much to even think about divorce. Last night was the first time the two of them had been together since weeks and she knew that he loved her just as much. He could be a LITTLE unfaithful, she knew the love between them was never going to change.

"Kyah~, Issei-sama!" Grayfia stopped death in her track when she heard that lustful moan coming from the inside of Issei's room.

Maybe she expected too much from her husband. This morning, she told him very clearly that if he wanted to fuck then he had every right to ask her to please him, anytime and anywhere he wants. She would be more forward with their sex life if he want, even when she was on duty like this. But clearly he didn't take her words very serious.

Grayfia kicked the door of his office opened and wasn't surprise in the slightest when found him fucking a maid from behind, with absolute ecstasy on her face.

"Grayfia." Issei managed to stop his hip from thrusting and gasped in shock when he found his wife standing there with a pissed off look on her face "Wait… this is not what it looks like, I can…"

But he was once again punched by Grayfia, with a fist flying at his face faster than he could come up with an excuse for getting caught red hand yet again. Issei was sent flying across the room and knocked out with just one, very powerful punch from his wife.

"You, out of here." Grayfia told the maid, trying to keep her voice as normal as it could. The maid quickly gathered her clothes and ran out of the room, not wanted to face the legendary Grayfia Lucifuge.

The silver haired maid sighed in disappointment and walked to her knocked out husband. She took him back to his chair and kneeled between his thighs, facing his still erected dick.

"You're impossible, Ise." Grayfia said and took a hold of his cock "But you're the man I love after all."

And she wasted no time in taking his cock into her mouth and proceed to suck on it

 _Line Break_

Issei Lucifer, formerly Issei Hyoudou just recently had a new hobby, fucking. However, as much as he loved to bang the life out of the girls, especially his wife, he still had his duty as a leader of an entire Faction with a lot of important duties. Currently, he was going through various documents sent by the remaining Pillars of Devil Factions, reading them carefully with the help of Grayfia before he could sign them.

Though, he couldn't help but keep a part of his mind wandering to a different topic.

It's a common knowledge in the World for a woman, or even women to be attracted by men who were charming and strong, especially the man who had both and even more than that like him. Before Issei Hyoudou's soul's fragments were inserted into Issei Lucifer's soul to bring the last Sekiryuutei back to life, women lusted after him because of his attractiveness and unmatchable demonic power. Now, combine with Issei's dragon like physique, phenomenon and traits, which had the same women-attracting power, the girls could no longer deny they wetted their panties the moment they laid their eyes on him.

Issei had to wonder if this was Ophis or Great Red's idea when they reset the world and replaced Sirzechs' existence with his, dramatically changing his life in a way he could only think about in his fapping dream. Grayfia was the one that was affected the most by this, as she had become the one who was spending the most time around him.

Also, unlike Sirzechs Lucifer who was too air-head and too uxorious to his wife, Issei Lucifer was never one who would stay still and let Grayfia led him around by his nose, never in a million years. Devil like him had every right to have a harem for himself, but because he was a Maou, he could only take one partner and make her his wife. In his opinion, it was just some dull shit the higher-ups came up to prevent the Maou to get too more power and influence than they already had. As a man's power also came in the form of the women of his harem, the only kind of woman who could join the harem of a powerful super-devil like him would be the most attractive, most beautiful and most powerful kind of woman, though Issei was never very picky about the girl he slept with, of course as long as she's beautiful and had large breasts. These women could raised a Maou's power as well as status seriously more than they already were and it could affect the voice of the higher-ups to the devil's society.

Like he fucking care about that. He was going to have the harem he always dreamed about as well as going to bang his girlfriend, Rias Gremory when she was old enough. He didn't care in the slightest if he was now her older brother, because it was only physically; mentally in his heart and soul he always loved Rias more than anyone else.

But recently Grayfia came very close, but that would be a story for later.

Anyway, insect wasn't that uncommon in Devil Noble Households, as many families wanted to keep their bloodline as pure as possible so marriage between brother and sister, aunt and nephew, uncle and niece weren't that strange to find in the past and even nowadays. Ddraig also told Issei about the girls' attraction to him. Because the world was resetted, Rias, Akeno and the other girls who loved him in their past life wasn't going to remember him or how they used to love a pervert-boy with all of their heart. However, it wasn't like he couldn't start over with them, because each girl would definitely feel strong attraction to Issei once they met him again.

Venelana gave birth to Rias two months ago and Akeno would follow after her King shortly after a month. The Church Trio and Kiba would have to wait for another year to reborn in this world while it would take Ravel, Gasper and Koneko two years to appear. Rosseweise, of course was still protecting Odin as his personal bodyguard.

He couldn't wait till the day Rias gathered them all once again.

 _Line Break_

A very naked Issei laid back that clearly wasn't his own, with a hand behind his head and a smug grin on his face. A head of long black hair that was tied into two long twintails bobbing along his big cock, slender fingers playing with his balls. His other hand tangled into the woman's hair, making sure that his cock always stayed connect with her mouth. Glancing down a little Issei couldn't help but smirk when he saw her large purple eyes staring at him, must be the whole time after taking his cock into her mouth. She had a smaller frame compared to his wife Grayfia, but it didn't make her naked body less sexy and erotic with her assets look way bigger than they already were, as her clothing had been dropped to the floor the moment he arrived.

Said woman was none other than Serafall Leviathan formerly known as Serafall Sitri, the current Satan with the title of "Leviathan" and Sona Sitri's older sister. She was the Satan in charge of foreign affairs and her most favorite affair was with him, her ex-boyfriend. Surprisingly enough, he used to date Serafall before falling in love with Grayfia during the Great War. The two of them were very close when they were young and started dating when they were teenager. However, when Issei and Serafall along with their friends Ajuka and Falbium soon got caught in the Great War and joined Anti-Satan Faction, their relationship never processed anymore than just a few kisses and cuddle. They were still very young back then after all.

But recently, a few years after the Great War, Issei, the real Issei Lucifer had decided to reconnect the two of them together in a way more than just two fellow Maou of the Underworld or two friends after finding out that Serafall still had some feeling for him. Issei had always thought Serafall was hot despite her childish behaviors, but after coming to this world and finding out what she could do to her lover and how she normally act on bed, Issei realized she could be as mature as anyone her real age.

The past two weeks since his arrival had been steaming for Issei, not just with his wife or the maids, but with Serafall as well. Grayfia, somehow knew about his relationship with Serafall as well, but in her opinion, it would be better if he got caught with a Maou rather than a lowly servant at his castle.

Basically, from two best friends and fellow Maou of the Underworld, Issei and Serafall had become sex-buddies. Like his wife, Serafall was very familiar with his size and even though she was small (make his cock look bigger), she pleased him like a pro and Issei also made sure to give her his all every time they were together. Serafall also couldn't help but notice some changes in her lover, as he was vicious in fucking her more than before but nonetheless she loved it.

After the grip on her head loosened up, Serafall let his dick slip from her mouth with a lewd popping sound, one of her small hands gripping the length she could barely fit in her mouth, beating it against his face before stroking it with a fast pace. "Neh neh, enjoying yourself, Ise-chan?" Serafall asked cutely, winking at him before sticking out her tongue to lick his cock from the base to the tip, earning a glob of pre-cum straight to her face "Ara, you're so mean." She giggled before wiping the cum away with her hand and smearing them around his hard dick.

"Oh man, Grayfia is going to be so angry when she find out I sneaked away from works again." Issei couldn't help but chuckle a little as Serafall went to work on his dick again "Don't you think?"

"Grayfia-chan seriously need to learn that she cannot hop you all for herself." Serafall released him and slowly crawled onto his chest, smashing her legs together to rub his cock with her thighs. "And you, Ise-chan, seriously need to know how to put her in her proper place, stop letting Grayfia from being aggressive towards you and what you want to do." Serafall then pressed her mouth against him and the two shared a passionate French kiss. His hands roamed over her body for a moment or two before he gleefully cupped both her tits, the firm, round, soft mounds filling his hands with plenty to spare "Not that I want you to treat her like one of your lovers, since she is your wife after all."

"Aw~, does Levia-chan care for her rival?" Issei teased, making Serafall pout. Though, the pout soon disappeared as Ise pulled Serafall up so her breasts would be right in front of his face. In his past life, he always wanted to at least touch Serafall Leviathan's breasts with his hands, but right now, here on her bed Issei could do whatever he want to do with them, as if he owned them…

Actually, he did own them.

Kissing along the tops of her huge tits, Issei kept his mouth and hands pussy with her soft fleshes. Serafall moaned out as the pleasure and rubbed her thighs together harder than before, squeezing his cock tightly in between. Despite her small frame, being one of the strongest devils the strength she was using could easily crush anything into paper, but it only brought him a great amount of pleasure. Issei then changed his target to the hard nubs on her chest, sucking and gently biting at her small, rock hard nipples, moving from one to the other and back again, holding her tits up and making an absolute baby hungry for his mother's milk out of myself with them.

Issei removed both of his hands from her breasts to put one on her ass, lifting her lower body up and the other on his cock, aimed it at her twat, slowly running the big head between her warm, soaking wet cunt lips. The brown haired man then slowly pushed Serafall's hip down, thrusting his hip up and slowly sliding his cock into her tight pussy. The both of them moaned out lewdly when Issei managed to sheathed his cock balls deep into her. No matter how many times the two of them had had sex with each other, Serafall's child-like body made herself simply too tight for him and his cock too big for her small cunt.

Issei would always prefer her older form, because her breasts were even bigger than her current form but a small body like this would make their fucking session become much more enjoyable and pleasurable.

"Aaahhh - ahhhhhhhh!" Serafall sighed in pleasure, her eyes going wide "Ah~ Ise-chan… you're so big~," she moaned as he slowly moved, sliding his dick in and out of her pussy with a gentle pace.

"Shit! You're so tight Serafall," he said to her, fucking her slowly and gently sliding five inches of his cock in and out of her fold

Serafall then sat straight up on his lap and impaled herself down his cock, moving her ass on his lap back and forth flexibly, her eyes had rolled back a little in her head and she was just moaning in time with his long, but slow thrusts and a smile on her face.

Issei then pushed himself up and they kissed, tongues sliding over each other as Issei wrapped his arms around her waist, cupping her ass and helping her sliding her pussy in and out of his length.

"You love this, don't you?" He asked her slyly, shoving his entire cock inside her pussy and holding it there, feeling her hot, tight and juicy cunt grip his whole length and her womb hug the bulbous head of his long dick "You love having my big fucking cock up your cunt, don't you?"

"Yes, I love it~!" Serafall moaned out "So good," she sighed and tried to move her hip "So fucking good." He started working my cock back and forth, fucking her faster and faster with each move he made, hands making sure to slam her hip into him to meet with his thrusts. Her slippery pussy lips were split wide by the girth of his cock, her cunt clasping my length tightly.

After getting a good pace to it, he speeded up his thrusts once again, shoving his entire cock in and out of her twat time and again, watching as her huge tits jiggled on her chest in time with their fucking. Serafall shot to her feet put both of her hands on his knees, bending her back and throwing her head back as she fucked her cunt onto his cock, their pelvises slapped against each other making wet and erotic sounds.

"Oh yeah - oh that's it, Ise-chan - ahhhhhh fuck." He stuffed his cock deep inside her, fucking her as hard and fast as this position allowing him. He had never had sex before in his world, but he was sure as hell that he would have cum his brain out but now he could go on and on until he wanted to cum, or could no longer hold it with his will-power. Serafall by now was cumming rapidly around his cock, her walls clamped even tighter around him, making it harder for Issei to keep the speed.

Soon, it became unbearable for the both of them and the two cried out with lust at the same time and exploded powerfully into each other. Giant wads of lava-like scum poured into Serafall's womb and soon, a creamy mixture of my juice and her vaginal secretions was forced out of her overstuffed pussy. The squishy noise of large amounts of sperm being squeezed out of her love tube filled the room. He stayed like that for minutes, his relentless cannon unloaded fresh seeds after fresh seeds into Serafall's sweltering pussy.

Serafall's belly swelled up a little at the amount of fresh cum he was bumping into her, but she loved it nonetheless. After he had stopped cumming, Serafall removed herself from his cock and dropped to all four again, cleaning his cock away from the mixture of her juice and his sperm with her tongue before taking the whole thing down her throat again.

Issei then pulled himself out of her mouth and flipped her around so that she was lying on her back. He then grabbed her ankles and pushed her feet all the way up to both side of her head, smashing her knees against her tits and sticking her ass into the air. Serafall giggled at the position she was pushed into, as Issei's muscular form completely towered over her, making she feel helpless underneath him like this. The Leviathan Maou cried out in both pain pleasure when Issei drove his cock into her asshole, his balls rested against her ass.

Issei bit the inside of his mouth to stop himself from cumming right there. Her pussy was tight, but her asshole was a whole different story, as he felt like his dick had been crushed inside of her anus. The pleasure was overwhelmed, but he managed to hold it in and move his cock slightly in and out of her to adjust to the pressure.

His dragon side would never let him become submit to any woman. It was always fucked them hard to satisfy his urge or marked them as his property.

"Not that I don't want it but… could you please be a bit gentle?" Serafall asked with a hopeful tone, however, the moment she saw his sly smirk she knew that her request had been denied.

 _Line Break_

Ever since coming to this world, his life was pretty simply, but very pleasurable. It was like a very challenging erotic adventure. Working as a Maou was pretty simple with a genius level mindscape so when he put his mind into it, he could finish mountains of paperwork in a few hours.

That was when all the fun started.

Since Grayfia had become more straight forward with their sex life, Issei spent much of his free-time stuffing her with his cock and filling her with his cum after giving her a nice pounding. Most of the time Grayfia didn't know what was going to happen to her, because Issei liked to catch her off-guard and see her struggle between the duty as his maid and the duty as his wife. It was fun to see his wife trying to keep her cool while having his cock in her mouth. With Grayfia's company, he no longer required his maids' service, which was a major disappointment for them. He was also spending more times with Serafall, adding the childish Maou into the list of his cock's worshipers right after Grayfia. He now had two women in his harem and was sure that they weren't going to be the only ones.

Other than the times he spent with Grayfia and Serafall, Issei also had some other thrilling moments to make his life even more exciting.

"Hey hey, watch where your hands are going ladies." Issei said, but didn't try anything to stop the two hands that went into his pant and placed on his cock, with slender fingers wrapped around the nine-inches flaccid dick.

One of those moments were currently happening right here, in his office.

"Ara, please don't tell me that you don't like it, Lucifer-sama." One of the woman said, with a small seductive smile. She was a woman with the appearance in her early twenties, with dark blue eyes and curly blonde hair, being done up very high with ornate hair decorations. She was wearing a pink dress that spoke very highly of her voluptuous body. The dress also had a very low V-cut to expose as much flesh of her generous cleavage as possible.

"Alright alright," Issei couldn't help but chuckle a little, allowing the ladies to have as much fun with his equipment as possible. Though, he kept his hands occupied with their melon sized tits, squeezing them in his palm with plenty to spare "What do you ladies want this time?"

"Oh~, I'm hurt Lucifer-sama." The other woman, standing at his left was a very beautiful with long black hair and purple eyes, her face greatly resembled Serafall, only a lot more mature and more seductive. She was also wearing a very tight fitting qipao with a large boobs-window, shamelessly exposing the feminine curves on her body, especially her big tits knowing just how much the man she was pleasing love tits "Do you really think that whenever we're here, playing with your cock like this, we want to demand something from you?" She pouted cutely "Seriously Ise-sama, you think so little about us."

"Is that so? So why are you two here then?" He asked, slapping both of their ass before lifting their dress up to grab their ass cheek.

"You know Ise-sama, sex with my husband have become very boring lately." The blonde woman whispered seductively into his ears "He is very small compare to you and can only last for one or two rounds before passing out, leaving me unsatisfied."

"I'm having the same problem with my husband too, Ise-sama." The black haired woman giggled "So after a long discussion with each other, we decided to come to you." Magically, his pant suddenly dropped down to the ground, making him naked from the waist down and giving the two busty ladies more access to his prick "So, Ise-sama, would you like to make us feel women again?"

"We promise to make it as enjoyable to you as possible." Their words made a grin appeared on his face

"Ladies," He finally spoke up and grabbed their crotch rather roughly, much to their shock "I think the two of you had come to the right place after all." Too horny MILFs, could he get even more luckier?

Both Lady Phenex and Sitri moaned out in lust when he inserted his fingers into their tight cunts.

It didn't take him long to move all three of them to his bedroom and the moment he was there, Issei was completely naked, his horse dick limped between his thighs but still more than capable of making both cougar moan in delight at the sight. The Sekiryuutei Lucifer smirked arrogantly and approached them, intending to make them just as naked as he was but Sera and Raven suddenly put their hands on his muscular chest together and pushed him to his bed, with his back leaned against the pillows.

"How about we make a show for you first? My lord?" Ravel's mother asked while licking her lips, climbing on the bed in a kneel position

"Why don't you sit and watch for a while, Issei-sama?" Raven said seductively, slipping her own shoes off and climbing on to the large bed with her friend. They knelt up together and hugged, their huge tits squashing against each other was the perfect sight for the booby loving man, with Raven's massive tits straining against the top of her qipao while Sera's pale mounds almost popped out of the top of her dress.

They kissed passionately, Raven's tongue diving into Sera's mouth as she reached up and pulled the top of her dress down, stretching the clingy fabric over her massive tits, freeing them so that she could finally get her hands on them. Not to be outdone, Raven tore open Sera's qipao, buttons flying off in all directions, before she pulled down the lacy cups of her blue bra. The two women gasped and moaned as they groped and pawed at each other's big, melon-size tits, squeezing the firm mounds that were much too big for their hands, tugging on their small, hard nipples.

Raven then reached down and pulled her friend's skirt up over her stocking tops and her pert ass, bunching it around her waist, one hand running over her ass cheeks, the other sliding down to her natural hairless cunt.

"Mmmmm, you shameless slut, not wearing any panties to meet your leader," Issei laughed at Sera, making her wink at him before moaning out as Sera eased two fingers between the hot, wet lips of her friend's pussy before pushing them inside ' _Hah, in your face Raiser_.' Issei thought with a wide smirk.

"We're expecting this, you know." Sera told him before moaning out "Ahhh, fuck - - oh that's good," she breathed, dipping her head down and licking at Raven's enormous jugs, sucking on her nipples in turn. She then reached behind her friend and fumbled with the button of her qipao and zip of for a moment before managing to push it down. Like Raven, she got to ran one hand over her ass and the other down to her pussy, sliding under her silk panties before she found the soaking wetness of her cunt.

"Ooooh, fuck me, honey," Sera breathed, spreading her legs as wide as she could with her skirt still round her knees to allow Raven's fingers easier access to her pussy. Raven raised her head and kissed her friend again, the pair of them working their fingers deep inside each other's pussy, their huge tits sliding together as they finger fucked their way to orgasm. Both of them panted as they kissed, pushing their cunts down on to their fingers, their juices running down their fingers as they shook, their pussies contracting at the same time as they both came to a shuddering climax.

"Uhhhnnggnnn, fuck, fucking hell, you're so good at this." Sera gasped, staring into Raven's eyes.

"You too," Raven sighed, pulling her fingers from Sera's pussy and licking them clean in front of her. "You taste good," she said.

"Want some more?" Sera asked, falling back on the bed, pushing her silk panties down, throwing it to Issei who caught it with a sly smirk and wrapped the soak panties around his cock to jack off. She spread her legs as wide as she could, her bald pussy wet and gleaming with her desire. Raven wasted no time and knelt between her legs, diving in to taste her friend's pussy, running her tongue up the folds of her twat before sucking gently on the hard nubbin of her clit. She slid two fingers back into her cunt, gently fingering her as she ate her out.

"Oh fuck - - fuck that's good," Sera sighed, reaching down and holding her friend's head in place. She smiled and looked up as she noticed movement beside her and saw Issei, naked, his huge cock hard and in his hand, offering it to her lips "Mmmm, got tired of waiting, my lord?" she asked.

"Suck!" He ordered and pushed the tip against her lips, forcing her to open her mouth.

"As you wish, Issei-sama." She tilted her head and licked around the massive bulbous knob of his prick, slipping it into her mouth and sucking gently on it, as she had sucked his cock more than enough to get used to the size. Issei leaned over her, angling his dick down, sliding more of his length between her lips, moving it back and fore.

"That looks so good," Raven said from between her thighs, watching Sera blow the young man as she continued licking and fingering her pussy.

"Want to share?" Sera asked her, licking Issei's cock. Raven slid up her friend's body, dragging her huge, round tits over her belly, pausing to lick and suck at Sera's hard nipples, before squashing her own tits against hers.

"You two really got the hang of this." Issei grinned as they kissed around the head of his prick, tongues swirling around the engorged knob before Sera gently pushed his dick towards Raven, which she took in her mouth and sucked gently.

"That feel good, honey?" Sera asked sultrily while fingering herself.

"Of course" Issei laughed, moving his hips as he slowly face fucked Raven.

"Want to fuck me? Want to fuck your auntie Sera?" From what he heard, Sera and Venelana, who was now his mother were best friend and came to visit Venelana at her residence at least three times per week and always brought gifts for the children, and soon she was called auntie by both Gremory Siblings.

"Didn't you come his here for that, slut?" Issei asked before saying loudly "On all four with your ass raise." He raised his power a little bit, but it was more than enough to make female devil like them shiver with excitement and arousal.

The mother of his secret lover almost wet herself at his commanding tone and power, feeling it wash over her like a tsunami of aphrodisiac. The woman soon obeyed him and got on all four with her ass raised as high as possible, shaking her bubble ass cheeks invitingly to the son of her best friend, who scrambled up on to the bed and knelt behind the perfect, upturned ass of his auntie. He parted her butt cheeks with one hand, using the other to guide his thick length between the sopping wet folds of her pussy, easing his big dick inside her.

"Mmmmm, Fuck! Fuck! It's too big," Sera gasped as Issei forcefully pushed his whole length deep up her cunt, knocking the wind out of her lung and made her gasp in surprise at the overwhelmed pleasure.

"Yes it is," Raven said from behind Issei as she wrapped her arms around his neck, pressing her large tits against his back "All the better to fuck us with," she kissed him on his lips before reaching around him friend and spanking her ass cheeks. "Fuck her, Issei-sama." she whispered into his ear "Fuck her tight little pussy!"

Issei thrust his hip hard and fast and deep, shoving all his meaty cock inside her with every movement of his hips, the big head spreading her pussy wide and punching into her womb. Sera felt her mature pussy rapidly clamping down around it, trying desperately to keep his cock trapped inside her as she gasped and moaned. The rapid ramming of his prick brought on another quick mind-shattering orgasm, triggering it deep inside her pussy, helped along by Raven who reached beneath her and strummed mercilessly at her clit.

"Awwwww Maou-sama! Fucking cumming!" Sera cried as her body shook rather violently, her huge tits quivering but they were soon caught by Issei. "You're making me cum so much~!" She moaned louder and louder as Issei kept fucking her, guiding her through her climax for a whole five minutes,. The super devil then withdrew his prick and let his auntie fall forwards and off to the side, grabbing Raven by the waist and threw her onto his front. spread wide, her juicy pussy on display.

She licked her lips as she looked at his massive cock, glistening with her friend's pussy juices. The blonde then spread her legs as wide as possible, her juicy pussy on display.

"My turn, Lucifer-sama?" she asked sultrily and spread her pussy lips. Issei walked forward on his knees, his cock bobbing and leading the way. Raven tried to reach out but Issei grabbed her wrist, stopping her from doing so with a cocky smirk.

"You forgot who is the superior here, Raven." Issei smirked and suddenly shot forward, pushing her down to the bed and plunging his dick into her cunt. The sudden penetration made Raven cried out and cum powerfully around his cock, her eyes rolled into the back of her head and her tongue lolled out of her mouth. Compared to his wife who could take his cock like a pro, these two still had a long way to go.

"Alright, let's fuck!" Issei said and started pounding into her, supporting himself on his hands as he slid his dick back and forth in her twat, sending it deeper with each thrust. He grabbed her legs behind the knees and pushed them back and up, spreading them as wide as he could, reared back and shoved his whole tool deep up into the mother of three children's cunt in one thrust before pulling back, his cockhead almost leaving her sopping pussy, and then driving forward once more. Over and over he did it, slamming his thick fuck stick into her as hard as she wanted.

"Oh fuck! Unngghhhh… ahhhh fuck yeah… fuck, oh my lord… big dick!" Raven gasped as Issei pounded her cunt mercilessly, fucking her as hard as he could "Fucking - - cumming!" she groaned, her pussy clasping his prick as she came. She shook and gasped as her orgasm washed over her, as he continued to pound his huge cock into her twat.

Sera sat at the side and watched Issei fucked her friend while she jammed three fingers up her own pussy, her other hand playing with her tits. Issei noticed this her and beckoned her over, pulling his thick cock from Ravel's cunt and holding it out to her.

"Taste her pussy on my dick, auntie Sera," he said, grinning like a maniac. Sera almost pounced on his prick, something her eldest daughter always did the moment she saw his cock, stuffing as much of it down her throat as she could, sucking and slurping Raven's fuck juice from his shaft. She mewled in disappointment as he pulled his dick free and turned her around, rearranging her so that she lay on top of Raven, their huge tits squashing together. As they kissed, sharing the taste of pussy, he spread Sera's ass once more and speared his cock into her, fucking her for a full ten minutes before pulling out and plunging his dick into Raven's pussy, giving her the same amount of time with his cock slid deep in her cunt before going back to Sera.

"Hey, you don't mind if I come into the both of you?" Issei asked as he felt his cock swelled up and his balls tightened up, ready to blow its load

"Go ahead, pump us full of your thick cum" Sera turned her head around and smiled at him

"You can impregnate us for all we care, we will be more than happy if we could bear your children, Lucifer-sama"

With that arousing green light, Issei gave Sera five more hard thrusts before letting go and filled her womb with a huge bucket of cum, causing her belly to swell up like a balloon and all she did was cum her brains out at the feeling of his seed being fucked into her. As his cum was forced out of Sera's widely stretched pussy, Issei pulled out and rammed his cock into Raven, filling her up.

"Ise-sama, dear, what is all that…" Then suddenly while Issei was still fucking the two sperm stuffed woman with his cumming cannon, the door of his room was opened and Grayfia poked her head in. The silver haired beauty looked at her husband and the two MILFs for a few second before widening her eyes and crying out in shock "ISE-SAMA!"

"Yo Grayfia!" Issei greeted her cheerfully as he finished the last dose of sperm inside Raven, giving Sera a hard spank on her ass before standing up with his cock coated in his own sperm "Is there anything you need?" He asked as both Ladies of Phenex and Sitri pushed themselves onto their knees beside him and licked his cock clean with their tongues, offering him their pleasure service right in front of his wife.

"Don't yo me Ise-sama!" Grayfia glared coldly at him "How many times do I have to tell you that among the group of women you can fool around with, these two are absolutely not listed there?" Issei pushed Raven and Sera's head away from his cock and started walking to Grayfia, his cock leading the way "Ladies of Pureblood Households are absolutely off-limited to you, what would happen if this got out or you accidentally impregnate them? Also, these two cougars only use you and your status to…" but she was silent when Issei claimed her lips with his mouth, snaking his hand into her dress to tear away her panties before spearing his cock into her cunt, making Grayfia's eyes shot wide open in shock at his sudden action.

"Lucky bitch." Sera Sitri muttered in jealousy while Grayfia was being bounced up and down on her husband's cock, literally lifting her feet from the ground every time he speared his cock up her twat "To think that she is the only one who gets to enjoy Lucifer-sama every time she wants to."

"Yeah…" Raven nodded her head before looking down at her cum bloating belly "Mind helping me with this?" She asked.

"I'd love to." Sera smiled and got to between her friend's legs, spreading her cunt and started drinking the flowing sperm inside.

* * *

 _ **End of Chapter 1**_

* * *

 _ **In the next update, Issei will get a sexual reunion with the ones that brought him to this sexy new world and help him take a step closer to his dream of becoming the Harem King…**_

 _ **Next chapter: Busty Dragon Gods.**_

 _ **READ and REVIEW**_

 _ **Ja ne!**_


	2. Busty Dragon God

**Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

* * *

 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one know about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

 ** _Issei Lucifer: The Harem King_**

 ** _Chapter 2_**

 ** _Busty Dragon God_**

[ **Timeskip- 2 years later** ]

Two years had passed since the day the world was resetted by the two most powerful beings in the world.

Once again, Issei found himself fooling around with a woman that wasn't his wife, having the appearance of an extremely beautiful woman in her early twenty's, with very long black hair and purple eyes. She had a body that even seductive being like female devil would die for, consisting of a massive melon sized tits with the ability to defy the law of gravity, full womanly hip with perfect waistline and a large, heart shape ass that went with a pair of long legs. She was sitting on his lap, facing away from him, dressed in a tiny black thong and matching color stockings, as her bra had been removed monster long before she got her hand on his cock and his tongue forced itself into her mouth.

Said woman was none other than Serafall Leviathan, his secret lover who took the appearance of her adult form, something that could drive any men mad with lust. Issei could barely believe his luck, because even in his wildest dream he could never believe that he could have a busty, silver haired woman as his wife and the most beautiful and attractive woman of the Underworld as his lover, who had always been the centers of his attention ever since the world was resetted.

As they made out passionately, Issei's hands roamed around her killer body before landing on her large firm breasts, the best pair of breasts in the Underworld in the palm of his hands and once again fell into his full mercy. Issei fondled them, kneaded them, groped them and teased her nipples… playing with her breasts in every way he could think of, loving their weight and softness within his hands. His cock was painfully hard in her hand, and had started dripping pre-cup from his cum-slit, but Issei chose to be patient and waited for the right moment.

"We should do this more often," Serafall moaned into his mouth, sucking on his tongue once last time before allowing her boyfriend to slide down "because two or three times a week aren't going to satisfy my need, you know." She giggled at the thought of having sex with him every day, but pouted slightly at the thought of a certain silver haired woman who was getting that very treatment "Grayfia-chan is so lucky, having you all for herself every night."

"Duh, she's my wife, she has every right to get fucked every day." Issei said as he pinched her nipples with his index and middle fingers, smirking slyly when Serafall's body shuddered with a mini-orgasm "But believe it or not, not every morning I wake up with Grayfia being the only one at my side."

"With something like this, I don't really think Grayfia can handle you all alone." Serafall said while licking her upper lip "Maybe I should visit your bedroom sometime, Ise-chan, a threesome with me and Grayfia-chan is something worth your time, isn't it."

"Damn right it is." The Sekiryuutei smirked but then groaned loudly when the feeling of horniness became unbearable. Gritting his teeth, Issei lifted Serafall up with his arms on her breasts and turned the both of them around, so he could place her on the bed with his cock positioned perfectly between her supple but cheeks.

Serafall giggled excitedly at her position and shook her ass against his cock. She was expecting him to do something like that, after all the foreplays and teasing she put him through.

"I don't know what about you Serafall, but I'm tired of waiting." Issei exclaimed and took hold of her arms, pulling his hip back a little before thrusting forward, slamming all fifteen inches of his cock into her wet and tight cunt. The moment his hips slapped against her ass Issei pulled back and started pounding away with reckless abandon, causing her to orgasm rapidly the instant he thrust into her womb.

"Oh fuck!" Her eyes rolled back and her tongue lolled out of her mouth as pleasure and orgasm washed through her body like a never ending wave of tsunami. With his arms linked with hers, Issei kept her upper body above the bed, at the same time he used his hold on her to pull her back to meet with his thrust, increasing the pleasure for the both of them and making her large breasts sway back and forth.

That was exactly how the next hour passed, Issei's hips never slowing down for a single second as he fucked his fellow Satan into a drooling mess, gasping rapidly and for air between mind shattering orgasms. After what felt like forever for Serafall, the pleasure became overwhelmed and Issei soon experienced one of the biggest ejaculation of his intense sex life, and the fact that Serafall allowed him to cum inside her made it all better.

"Take my load Serafall, take it all!" Issei grunted lustfully while stroking his cock as fast as he could, shooting his cum all over her face and breasts after stuffing her womb could no longer handle it and began to spill out. Soon enough, Serafall pushed her head forward and sealed her lips tightly around the base of his cock, allowing him to dump the rest directly into her belly.

"Remind me why I broke up with you again." Issei breathed as he leaned his body back slightly, his cock was released from her mouth and was then resting on her face, forcing her to inhaling nothing but his musky scent.

"You thought Grayfia had a better pussy for you to fuck," Serafall giggled "Which, was totally wrong, by the way." She pushed her lips out to kiss his cock.

"Tch tch… I wasn't wrong, but not right either." Issei grinned and moved back a little to grab both of her ankles, getting her into position for another round "Now, let's continue…" However, before he could finish that question, a flash of light suddenly engulfed his body and teleported him away before he could realize it.

In a blink of an eye, Issei widened his eyes in surprise when he found himself standing in the middle of the Dimensional Gap, the endless void where in every direction there was a mix of iridescent colors, the home of the two dragon gods Great Red and Ophis, the two most powerful beings in the world.

"Ddraig" Issei said to his partner while looking around "Do you see what I am seeing?" he looked down and widened his eyes at the red, scaly ground he was standing on, which was none other than Great Red's gigantic body, his back to be specific.

[ **Yes partner** ] the legendary heavenly dragon replied instantly [ **We're in the Dimensional Gap. Great Red and Ophis must want to meet you** ] the brunette man nodded his head in agreement. After two years without hearing anything from them, Issei was very eager to meet them so he could give them his gratitude for allowing him to have another, way better chance in life, something that he could only dream about. Instead of doing crazy moves than usual, Great Red was flying rather steadily inside the endless void rather steadily, allowing Issei to stand on his back without any problem.

Issei then made his way to Great Red's head, the place he believed Ophis was waiting for him at. He was still totally naked, but at least his cock had softened and dangled between his thighs, and that shouldn't be a problem. Ophis was pretty naïve, and she had little to no modesty.

Plus, it was her fault summoning him to the place while he was having sex with Serafall.

Soon, he found her, but much to his surprise, she didn't take the form he expected her to be "Greeting Issei! " Greeted the Dragon God with a smile, looking at Issei's naked body from head to toe "I see that our new world is treating you very well." He could recognize her immediately, despite her appearance was slightly different, something that was exciting him to no end point.

Ophis was no longer a cute young girl, as she took on a more mature appearance of her former appearance, being an extremely beautiful young woman with extremely long, wavy, straight black hair, grey eyes, with pointy tips ears. Her outfit consisted of a knee-length, gothic lolita dress that left everything from her neck down, including her melon-sized breasts completely exposed, her nipples covered only by black dug-taps. She wore no panty, so her pussy lips were pretty much visible.

"Ophis?" The black haired woman nodded her head, making him grin "Yeah, it's good to see you again." He smiled at her, trying his best not to get excited by such voluptuous woman. He was in the present of two powerful beings that could make his existence completely disappear with just a flick of their fingers, so it would be better if he behaved himself "I like your new appearance, by the way."

"It suit your taste, doesn't it?" She asked, tilting her head to the side "Big breasts, beautiful and attractive." He didn't know how much Ophis could change after the world was resetted, but from the way she was looking at him, he could tell that she wasn't as naïve as she used to be, which was a good and bad thing at the same time.

"Yeah" Issei grinned before bowing his head to both of them "Ophis and Great Red too, thank you, for giving me this second chance!" he said gratefully and heard Great Red made a loud grumble, something that Issei could translate into ' _Yeah, no problem_ '.

"I only help you keep your promise to me, Ise." Ophis approached him and put a hand on his shoulder "Return to the house of Sekiryuutei, together." Her gigantic breasts were so close to him that he couldn't help but stare.

"Well, my life is not exactly what I thought about, but soon in a few more years, it'll return to the way it used to be." Issei nodded his head "But is it necessary to reset the world like that? Not that I'm complaining by the way."

"Your soul were damaged beyond repair, " Ophis shook her head "but fortunately, Great Red was near, and asked him to help you. We managed to keep your consciousness and memories from being destroyed by Samael's curse. By combining those fragments of your soul with someone else's, you will be brought back to life, but I doubted you would want to live with someone else body, wouldn't you?" Issei nodded his head with a small chuckle at that "And so, we decided to reset the world and the entire timeline, interfering with some events in order to make you better, stronger and greater but most of all, to give you a different, better life than before. I kept your soul inside Ddraig's armor, and waited a couple of millenniums for the new you, the new Issei at this new timeline, to be born to fuse you with him."

Issei made a embarrassed smile while scratching the back of his head "Kind of feel bad for Sirzechs-san but… it can be helped" It was the only thing he could say. With Ddraig's help, he had come to accept the fact that Sirzechs' existence had been erased from the history forever a long time ago.

"Some sacrifices are necessary for the greater good." Ophis stated calmly, squeezing his shoulder gently "Not just for you to keep your promise, but in the upcoming war to prevent the awaken of Trihexa as well. I don't like Great Red, but at least he is willing to share the Dimensional Gap with me. Trihexa, on the other hand, should stay dead."

"I understand, Ophis." Issei nodded his head, but then smiled when he decided to change the topic "Either way, it's good to be back."

"I have been watching you ever since you were brought back, Ise, and I must say I'm extremely amused and interested in the way you've been spending your times for the last two years." She then paused for a second before saying "What a dragon you have become! Even Great Red is impressed at the way you take your mate."

The Sekiryuutei blushed a little after that, and scratched the back of his head while smiling nervously.

"W-well, I have to get into character, haven't I?" Issei Lucifer, after all, was a playboy long before his arrival.

"All you need are a tail, a pair of wings, dragon scales and a horn to become a real dragon." Much to his surprise, she grabbed his semi-hard cock "This part, however… is indeed something belong to a real dragon." A grunt escaped her lips when Ophis squeezed his length playfully "You've been putting this into good use, haven't you?"

"Y-yeah…"

"Don't take me for a fool, Ise." Ophis poked him on his chest and said with a seductive tone "In my past life, I wanted nothing more than to get rid of Great Red and return to the Dimensional Gap, and kept my sole attention on the subject. However, after we resetted the world and came into an agreement of sharing the place, I was about to experience more about the world, especially human life." Ophis licked her lips in a seductive way, something that if Issei didn't know any better he would think that it would be impossible for the honest and naïve Ophis to do, before removing the duct-tapes that covered her nipples, showing them to him much to his shock.

The man gulped nervously at the sight of her tempting, pink nipples. Her complete exposed breasts made his cock hard in seconds.

"Ise, do you want to repay me for giving you your new wonderful life?"

"Of course!" Issei nodded his head rapidly at her question.

"Good, have sex with me." Issei gasp in shock "I'm very interested in doing it with you, especially after spending two whole years watching the porn you now call your life. Plus, only a dragon can satisfy a dragon, so I don't think anyone can do it better than you."

"Are you… serious." He asked in disbelief, and grinned broadly when Ophis nodded her head "Fucking awesome!" he cheered, taking a step forward and pressed his lips against hers, kissing her with passion before inserting his tongue into her mouth and played with everything within her oral entrance.

Ophis was rather surprise by his action, but soon she found herself enjoying her first kiss a lot and returned the favor by licking his tongue and kissing back.

Making out with a busty dragon god on top of the head of another, Issei could barely believe his luck. His hands moved to her breasts and the Sekiryuutei could barely believe how soft and good her breasts were in the palms of his hands, making her moan for the first time into his mouth.

[ **Ahem!** } Ddraig cleared his throat and spoke up while Issei was still making out with his new lover [ **Can believe I'm going to say this, but damn I'm jealous with you, partner.** ]

Issei chose to ignore his partner for the time being, before he was too focus on the feeling of Ophis' soft yet incredibly firm breasts to muster a proper reply. As his hands played with her nipples, his mouth pulled her tongue out of her mouth when their lips separated, as he started sucking on it with earnests. With his experience, he could tell that Ophis was the kind of woman who knew what she was doing, probably from watching his lovers having sex with him so many times, but she did it in a rather sloppy way, meaning that it was indeed her first time.

All the better for him to take charge.

"Great Red won't mind, will he?" Issei asked, pulling back while his hands were still molding her breasts in all shape possible "Us fucking on his head like that?" he asked

"Don't worry, he's too big to actually hear or know anything." Ophis shook her head reached her hands down to spread her pussy lips "Put it inside me." She said, looking at his cock "Reshape my pussy with your cock." She purred, trying her best to be seductive.

"Seriously? No foreplay? You sure?" Issei asked in amusement but in the end, he did what she told him to do, starting by inserting the tip of his cock into her inside before grabbing her ass cheeks, using them as handhold to plow his cock into her pussy, fucking her in a standing position. Both Issei and Ophis moaned out loudly when their hips smacked against each other together, her buttocks deforming in his grip. His massive cock slid into her pussy with no problem, and yet she was even tighter than a virgin, clenching tightly around his length and making it hard for him to start moving.

There was no hymen, which he decided not to ask about.

"Ah! So this is how sex feels like?" Ophis moaned and hugged his head into her massive bosom "Do it again, Ise!" Issei pulled his hip back, letting out a pleased moan as the bulbous head of his dick nearly slipped out of her inner folds before thrusting back in. Ophis smiled dreamily when pleasure washed through her spine and rolled her hips in excitement for more. Her eyes crossed and her mouth dropped open in a 'O' as her brain was soon overwhelmed from the overload of pleasure sent to her mind after Issei managed to pick up a decent speed.

"Fuck! Your pussy is the best Ophis." Issei moaned into her breasts, increasing his pounding speed to a whole new level.

"Sex feels so good!" Ophis kept moaning, with drool running down the corners of her mouth "I love sex! I love sex! Fuck! Fuck!" She reached her first climax ever, which caused her body to shake and quiver in pleasure. The way her pussy tightened even more around his dick became too much for him to handle, and his knees gave out first, as he collapsed to his back with Ophis on top of him.

"Well shit!" Issei grunted, his cock buried completely inside her womb and made her orgasm for another full minute. Smiling widely, she pushed herself up and placed her hands on his shoulders, raising her hip a little before slamming herself down, allowing his cock to spear into her womb. It wasn't long when Issei felt Ophis's inner walls once again clamped down on him like a vice, her body shook for yet another mind-blowing orgasm.

It wasn't long before Issei's dragon instinct kicked in, preventing him from letting the female dragon god to have all the control. With a devious smirk, Issei swiftly changed their position, with his cock was still deep inside her pussy. Ophis let out an undignified yelp when she was suddenly rolled around and found herself beneath him.

Issei then drew his hips back, pulling his shaft out of her until it was almost entirely out and thrust it back in her repeatedly, pounding the sexy dragon god into the hard scales on Great Red's head, who from the look of it, was still obvious of what was going on. The super devil quickly leaned down to press his lips against hers in order to suppress the pleasured cries.

He smirked into the kiss as he saw her eyes roll up to the back of her head and orgasmed crazily around his fifteen inches cock. It wasn't long before the result of her pussy clenching on him, and then cumming for what appeared to be a dozen amount of times, had effectively made him cum as well. Taking a moment to just enjoy the moment of filling the womb of the Ouroborous Dragon God herself, Issei then released her lips and standing straight up, smiling at the face she was making, with her eyes glazed over, her mouth opened with her tongue hanging out like a panting dog.

The powerful super devil giggled perversely as he filled his palms with her oversized, yet perfect tits again, thrusting his hip slightly to increase the pleasure his climax was giving him. As soon as he finished cumming, Issei pulled his cock out and grinned at her swollen belly, hoping that he didn't knock her up, because a child between the most powerful devil and the dragon god would be a really big problem to the world itself.

"I've done it." Issei muttered proudly while pushing his chest out in pride "I fucked Ophis, the most strongest being in the world." And stuffed her with so much cum that she looked nine month pregnant. His attention was drawn back to Ophis after she took his cock into her mouth and sucked as hard as possible, popping her head up and down rather skillfully for a first timer like her "Oh yeah." He grinned, nearly forgot that a god, formerly a virgin or not, like her would never go down that easy.

* * *

 ** _End of Chapter 2_**

* * *

 ** _Yagami's note: There's done, another chapter delivered, a chapter that is basically no foreplays at all, but it can't be help._**

 ** _After going through some serious thought, I couldn't bring myself into writing a female Great Red, it's simply too weird for me to write. I've never written gender-bender before, so I don't think I can really do it, since Great Red is originally a male._**

 ** _Next chapter: Another five years timeskip and the introduction to one of Issei's wildest dreams: A peerage full of busty women… well, it's not full yet in the next chapter, but Issei will have only girls in his peerage and of course, Grayfia is his Queen. The girls who are going to appear in the next chapter are all coming from High School DxD._**

 ** _But of course, the rest of his peerage, aka harem will be opened for suggestions, so vote and there is no limitation of which anime/manga they are from!_**

 ** _Next Chapter: Peerage Mayhem. (Featuring the legendary 300 Issei.)_**

 ** _And It is going to be a super long chapter._**

 ** _Read and Review_**

 ** _Ja ne!_**

 ** _P/S: I'm thinking about opening my own Youtube channel, what do you think?_**


	3. Peerage Mayhem

**Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

* * *

 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one know about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

 ** _Issei Lucifer: The Harem King_**

 ** _Chapter 3_**

 ** _Peerage Mayhem_**

[ **Timeskip- 5 years later** ]

His past goal was to one day rise to the rank of a High-Class Devil so that he could gather his own servants and create his own harem, a peerage that would consist of nothing but beautiful and attractive girls with big breasts, becoming the "Harem King". However, after the world was resetted, creating a whole new timeline that was similar yet completely different from the old and he was brought back to life with the identity of Issei Lucifer, a super devil who was known as the devil's sex god among the high-class society, Issei realized that there was no point of chasing after that dream anymore, especially when he was, in a way, the Harem King.

However, while he could have any women, Issei decided to keep his dream of creating a peerage that would consist of nothing but big breasts beauties, because five years ago Grayfia was the only servant he had in his peerage, and to say he was shocked after learning that was an understatement

Fucking around wasn't the only thing he did every single day. With the memories of the future, his power as the Maou of the Underworld, Issei was able to interfere with some of the more important events before it could happen, altering the future for the better and saving many lives.

One of them being the naughty kitty cat who kneeled between his leg under his working desk, meowing lewdly as she fingered herself while sucking on the best cock in the Underworld, drinking a nearly endless supply of hot milk directly from its source. She had become of his main distractions ever since she gave herself to him mentally and physically, becoming the first Bishop of his peerage, and was none other than Kuroka, the sexy and mischievous Nekoshou who used to want to carry his children in the old timeline.

At the new timeline? She wanted him to breed her. She had been in that position for the last two hours, continuously gulping down his sperm while sucking on his cock, serving her new master with the best of ability.

Issei found her three years ago, wandering on the street of the human world, trying to fend for herself and her sister after their parents passed away. He took her in before the high class devil who turned her into his servant, the one that she killed became Underworld's most wanted criminal for it in the old timeline, could get to her first. It took Kuroka sometime to trust him, but Issei had shown her nothing but kindness and after six months of living at his palace, Kuroka chose to become his servant to repay what he did to her and Shirone. Issei used one Bishop to reincarnate her into a devil, and barely a day later he had her on his bed, both outside and inside painted white with his cock.

Shirone became great friend to Rias, who came to play with her every weekend. Both of them loved him a lot, but he still couldn't show anything other than brotherly love to them, since they were still too young.

Since then, she had become one of the more regular occupations of his bed, after Grayfia and Serafall, the later wasn't very happy of course, but it wasn't like she could say anything, especially not after she found herself pregnant with his child, a son that she gave birth to nearly ten months later. Issei decided to name him Millicas to honor the memories of Sirzechs within his mind. He was his son, yet his personalities were just like the original Millicas, which wasn't a surprise because Grayfia was the one who raised him to become a well-mannered boy, after all.

He wanted to help Akeno as well, but had to wait for the right moment because she was still living happily with her parents. Kokabiel was still around, so he couldn't just approach Rias' future Queen and her mother, Shuri Himejima and offered them his protection like that.

Back to the current matter, with half of his cock still inside of her mouth, Kuroka slid forward, lifting herself so that her huge jugs flopped all over his cock. The cat girl then took both of her breasts into her hands and wrapped them around his cock, causing Issei to moan as they firmly gripped him. Kuroka moved her chest from left to right, pushing herself onto his cock, fucking it with her soft fleshy mounds. Her hands beat faster and faster, jerking him off, ramming it into her tits while still sucking on the big bulbous head of his cock.

"There done!" Issei grinned as he finished the last paperwork of the day and leaned back against the headrest of his chair, grinning like an idiot as he came into Kuroka's mouth for the third time in two and a half hours. It lasted for fifteen minutes, and when he was done, Kuroka pulled back and licked her lips with a playful smile.

"Did you enjoy my service, Ise-sama nya?" Kuroka asked, lifting his shirt up and mashed her breasts against his diamond hard abs with his big cock poking out between her breasts, her hard nipples poking against his skin.

"Well, did you enjoy your milk?" He replied, smirking lecherously as he removed her Kimono, leaving her completely naked and lifted Kuroka up and lay her on the table so that her legs dangled off the edge and her butt was sticking upwards. "I hope you did, because it's time for me to truly enjoy your service myself."

Issei said and slammed his cock into her pussy, thrusting himself into her at a jackhammer pace. The table shook, the documents fell over as Kuroka was jerked back and forth by Issei's violent thrust. Her weight centered on her tits, her body pivoting back and forth on the flattened globes, helpless against the onslaught of Issei's immense shaft. Kuroka was groaning as she had one orgasm after another, then he stop and pulled out halfway, just resting there.

"Phew! Sorry, can't help myself." Issei chuckled as he slapped her ass.

"Shit! Shit! Shit! Can you be a bit more gentle at the start master?! You're tearing me a part!," Kuroka groaned, but her pussy said otherwise by tightening around his dick, even making it harder for him to move.

"Why should I?" Issei ask smirking down at her, wrapping her tails around his hand and used them to pull her back the same time he thrust his cock forward, going as far as he could into her "Also, you love it, right? You love to have your vagina torn apart by your master's dick, don't you? " She moaned as he pulled his cock back a little before thrusting forward again, pushing his cock all the way in until the head took it place inside her womb, his balls slapped against her thighs and hip smashed into her supple ass cheeks.

Kuroka seemed to be cumming constantly as Issei using his hands stoke and kneeled her breasts with one hand while the other was playing with her voluptuous body. Kuroka was cumming like crazy on his thick shaft, constantly moaning into the air as his powerful manhood continued to overloaded her senses. As he just kept up the fast pace until he felt the addictive feeling of the sperm shooting up from his balls, causing his cock to jerk as it deposited more cum in her pussy then she'd ever had before.

Kuroka screamed from a tremendous orgasm when he came, her belly swelled up like a water balloon as Issei poured his juices into her. Her eyes and mouth flew open as she was swept away by the waves of orgasmic pleasure washing over her.

While cumming his fourth orgasm of the day into her pussy, Issei didn't bother to look behind him when there was a loud roar of a blue western dragon that was flying toward the direction of his office, heading to one of the open windows. When it was close enough, the dragon's body suddenly shifted and changed into a more humanoid shape, taking the appearance of a very beautiful woman with beautiful pale blue hair and matching color eyes, wearing a silky light color dress that hugged her body like a second skin and a large, white coat with light blue fur trimming around the neck and the sleeves' edges, draped over her shoulders like a cape. The woman flew through the open window and gratefully landed her heels down to the floor of his office, her large breasts jiggled at she did so.

"I see that you're enjoying yourself again, Lucifer-sama." The Chaos Karma Dragon and one of the current five Dragon Kings, Tiamat greeted him with a smile on her face and a slight bow of her head. She was completely unsurprised by the sight before her, because it had become something very normal since the day she became his servant, two and a half years ago.

"Oh hey Tiamat, welcome back." Issei greeted his Rook with a smile and pulled his cock out of Kuroka's well used pussy and allowed her to get down to her knees before him to clean his cock with her mouth and tongue "You know, there is a door over there, you should try to use it sometime?"

"I like the window, and flying more than walking." Tiamat walked to him and when she was close enough, she pressed her lips firmly against his to give Issei her a hot and passionate French kiss, something the new timeline's Maou Lucifer happily welcomed and returned with just as much passion.

Two years ago, Tiamat summoned him for a sexual request after she overheard a conversation about him by coincidence between two high-class ladies while she was watching the second semi-final match of the Rating Game Tournament, about him being the Devil Faction's sex god or something like that. They also compared him to a dragon. After getting a summoning contract for herself, Tiamat summoned him and wished to have sex with him, hoping that he could give her the best one night stand ever.

Let's just say that after he was done with her, it was no longer an one night stand. For the next few weeks, Issei found himself fucking Tiamat any time he got the chance to, either at his place or her place. Sex with her was incredible, because she had the stamina of a dragon but unlike Ophis, she had a lot of experience in said matter and literally blew his mind with pleasure, and soon he realized that he needed her in his harem.

Issei decided to challenge Tiamat for a mock battle and made a wager with her. Because the service of someone like at his status wasn't cheap, even someone like Tiamat could barely effort it for too long, so if Tiamat won, she would have his bedroom service for free. However, if he won she would have to become his familiar and had to become his lover forever.

Basically, it was a win-win wager for the both of them, but the way dragons viewed their lovers was very different from the other species, and seek domination over their lovers whether they were a male or female. Like many dragons, Tiamat was a aggressive lover on the bedroom, and it's really hard for him to keep her at the place he wanted, so he wanted her to become his familiar, hoping that the new difference in status would make her submit to him.

It was a tough battle, possible his most intense battles ever. Issei couldn't use Boosted Gear or Ddraig's help to aid him in the battle, because it would probably get him into a lot of questions as well as troubles afterward, so he had to rely solely on his new power, the Power of Destruction. While it was a devastating power, Tiamat stood her own ground against him and fought for a chance of domination like a true dragon, holding nothing back.

In the end, Issei came out with the win but not after tearing the dimensional battlefield apart with his final form, Aura of Destruction, and shook the entire Underworld with raw power (It was the first time ever Issei used that form Sirzechs was so famous about and he was completely terrified at its power, because it took him only one blow to defeat Tiamat). After the result was decided and Tiamat admitted her defeat, Issei tore what was left of her clothes to shred and fucked her stupid right in the middle of the forest, claiming his trophy right on the spot.

However, in the end, Issei decided to make her his servant instead of his familiar. Because he believed that she would have more uses to him as a servant than a familiar. Tiamat agreed with it nonetheless, and became his Rook after he used a mutation Evil Piece to turn her. Tiamat was granted the title of the most powerful Rook as soon as the news were announced, and had been living with him since then.

"Well, shouldn't you finish you work first before thinking about having your way with one of us? Grayfia won't let you get away with it this time, you know." She asked after pulling back from their kiss.

"Don't worry, I have already finished all of them." His hand shot out and grabbed her breast suddenly, causing Tiamat to moan out loudly.

"That's great, because I'm in need for a good fuck." She then looked at Kuroka and removed her from his cock, replacing Kuroka's mouth with her hand, much to her annoyance "Sorry dear, but I believe you've already gotten enough for the morning." Before Kuroka could say anything, Tiamat put her free hand on Kuroka's head and rubbed it gently "Don't worry, I will return your master to you as soon as I have my fill of his sperm." With her grip on his cock, Tiamat pulled him with her as the two of them walked out of his office and headed to her bedroom.

"Kuroka, clean the table for me alright?" He told her before existing his office.

"Yes, Ise-sama nya." She nodded her head and quickly went to work, though with a little trouble because his sperm kept flowing out of her pussy and made puddles of cum on the floor.

The trip to Tiamat's bedroom was rather eventful, because many maids saw them and giggled at the state he was in, which Issei could only shrug his shoulders in response and allow Tiamat to lead the way. The thought of fucking her right in the middle of hallway with so many spectators was rather tempting as well.

It didn't take them long to get there, and as soon as the door was closed, their mouth once again slammed into each other, hands roaming around each other's body. Issei removed her cloak and easily pulled down her dress, leaving her completely naked in his hand before letting her do the same to him. Issei put his hand on her ass and lifted her up, getting her to sit on his cock with her legs wrapped around his hip, arms around his neck and tits mashed firmly against his chest. He then turned them around and pinned her against the wall, with enough force to leave a crack, letting go off her lips before kissing down to her neck.

"Oh yeah, suck on that my lord." Tiamat moaned as she threw her head back and moaned in pleasure when Issei took her hard nipple into his mouth, her fingers through her master's hair "You love it, don't you?" She knew about his fetish for breasts, and was very glad that hers were among the biggest of his lovers, surpassing even his way by a solid cup, as both were double F-cup in size.

Issei then slid his way down Tiamat's body, with a groan of desire he ignored the thought of teasing his way down her body and simply buried his face between her legs, attacking her cunt. His tongue was exploring her folds while his lips pressed tightly against her outer lips, causing her to moan as her entire body shook with climax. Tiamat sat there with her legs rested on his shoulder, a blissful smile on her face as her master ate her pussy and drank her juice with earnest, groping her own breasts and twisted the nipples to have even more pleasure.

Still in the same position, Issei stood up suddenly, making the female dragon king make a sound in surprise and held onto his head to prevent herself from falling down. Just like that he carried her around the room before throwing Tiamat down to her bed, grinning perversely at the way her tits jiggled around.

"It's time for you to return the favor, Tiamat." Issei said and made a gesture to his gently throbbing cock. Tiamat smiled seductively and crawled on all four toward him, making sure to add in some extra sways to her girls before putting her hands on his hip and placing a kiss on the tip of his aching cock.

The busty woman then took the head of his cock in her mouth and teased the tip. Hearing the groan of pleasure, Tiamat started pulling him deeper, pushing the head into her tight throat, her tongue wrapped around the shaft a few times, allowing her to tease him as his cock was shoved down her throat. His cock was probably the biggest cock she had ever swallowed down her throat and she had always enjoyed the challenge of swallowing him all the way to the root, something she was sure not many women could do because of the size and length.

"Oh fuck!" Issei moaned as he felt her throat massaging his throbbing cock, struggling to stay standing as his Rook started fucking his cock with her throat, moving her head back and forth on his prick, humming a tuneless melody as she did so "I'm cumming Tiamat!" Actually, she really didn't need him to warn her because his cock suddenly swelled up in size and pulsed rather strongly inside of her throat. Tiamat then pulled back to keep just the head in her mouth, starting to stroke his cock with both hands as the first dose of sperm flooded her mouth almost instantly, hitting the back of her throat hard. Spurt after spurt of thick cream then shot into her mouth and Tiamat was forced to swallow as fast as she could, and she barely had a moment to savor the taste of his fresh cum. Minutes later when it finally tapered off, She gave him one last good suck before pulling off his cock with a loud pop, smiling as she beat it against her face.

Issei grabbed her head with one hand and pulled her up so he could crash his lips against hers, kissing his dragon lover passionately while her hands kept stroking his cock. After he got his fill of her tongue and saliva, Issei pushed her down to the bed, lying on her back and grabbing Tiamat's legs by the ankles and spread them eagle as he pushed them forward till her knees where nearly by her head, putting her ass up into the perfect position for him to plunge his dick into her ass, burying inside her to the hilt, smiling lecherously as his hips smashed against her heart-shape ass. With his grip on her ankles, Issei leaned over and started to pound her tight ass with long hard strokes, rocking her body with his oversized cock.

For the next hour, Tiamat just laid there and let her mate had his way with her ass while motorboating in her cleavage, enjoying the great pleasure he brought to the both of them with her eyes shut tight, trying her best not to make the shameless Ahegao smile like most of his lovers.

Then, with one final thrust into her asshole, Issei let loose a primal cry of pleasure, almost like a much smaller but wasn't any less mighty roar of a dragon and released the climax he had been holding erupted deep inside her. Issei filled his lover with his thick cream, causing her stomach to bloat out from the sheer volume of it. After a while, finally spent, the Maou slowly withdrew his rock hard prick from Tiamat's gaping anus, allowing the cum he dumped inside her started pouring out of the poor woman's stretched asshole. Giving her ass a hard slap Issei climbed on the bed and straddled her head between his knees, putting his cock into her mouth and going down as deed as he could, forcing Tiamat to taste her own ass on his cock. He stayed like that for a solid three minutes before pulling out, grinning in satisfaction.

"Well, that's satisfying indeed." Tiamat smiled and placed another kiss on his cock, which was resting on her face "You're still up for more, aren't you?" She asked teasingly, and was hit in the face by his hard cock.

"Are you really asking that?" Issei grinned and lowered himself down until he could feel her pussy against the tip of his cock. "Let's continue this, shall we?"

 _Line Break_

"Ise-sama! What are you doing?!"

"Spending some time with my wife, of course."

"I'm working…"

"Like I care."

With a strong grip, Issei lifted Grayfia up and onto his back, her legs splaying over his shoulders and walked into the master bathroom. It was half past eight in the evening and Issei just returned from an important meeting about the recent conflicts between some high class devils with the fallen angels of Grigori. As soon as he returned home Issei was greeted with the tempting sight of his wife in her usual French maid outfit, standing in the middle of hallway giving orders to the other servants of the place, looking as perfect and fuckable as always.

She was so perfect that he couldn't help but wanted to mess her up, especially her inside.

Pushing open the doors to the shower of their bedroom, Issei removed his clothes and did the same to Grayfia much to her protest, kicking them away before closing the door and turning on the water from the multi shower heads. Before Grayfia could make any more protests or even worse try hitting him, Issei pressed her body against the tile shower wall, her toes dangling a foot off the ground so he could see her at eye level. Issei kissed her with such suction that her head popped forward, her lips mashing against his. She tried to resist at first, but after a minute Grayfia melted into the kiss and returned the favor by kissing back with as much passion, wrapping her arms around his head to kiss him as hard as she could.

His hands traveled to her back and unhooked the hook of her lacy bra, forcefully pulling back from her lips to remove the wet undergarment from her body before moving his hand down to her sexy thong, plucking it like a guitar string, before he dropped to his knees, his hands holding her upwards, as he slid the thong off with his teeth. Issei then kissed her between the legs, burying his face in her neither lips, causing Grayfia to groan in pleasure. His cock arched with need, but his wife's pleasure came first, and didn't let go until she cum into his mouth.

When Issei stood up again, his solid fifteen inches cock slid between her thighs and pressed its mushroom cap head against her pussy lips with a rub that triggered a simultaneous groan from both of them.

"Thrust it in honey!" Grayfia moaned as she looked into his eyes "Put it in and fuck me good"

Dragon or not, it was an order he couldn't stop himself from obeying, thrusting his cock inside her with a grunt. Grayfia hissed through her teeth as her husband stuffed her, her entire body swayed with the feeling of his dick in her. Issei then released his grip on her waist held her up by his monster cock. Groaning, Grayfia put her hand on his shoulder and shook her body up and down on his cock, rapidly screwing herself on the massive prick that she loved so much, moaning and whimpering in pleasure as she rode him with earnest.

At last, his hands came back to her body, one on her hip and the other on her large breasts and started thrusting all by himself. His mouth moved to her neck and kissed his way to her jaw, nipping on Grayfia's soft and flawless skin, crashing his hip against hers over and over, and she bucked and rocked against his muscular body ferociously. Grayfia came with a cry, squirting her juice around his cock, her insides shuddered and clenched even tighter around his prick.

At last, Issei announced his hot release with a lustful yell. The moment he came her cock-stuffed womb burst like an overfilled balloon, as if her insides were being blasted with a machine gun that fired dollops of sperm instead of bullets. After thirty minutes of non-stop cumming, Issei removed himself from her with a pop sound, his warm sticky goo clinging to her inner walls between her legs, but most flowed out and fell to the wet floor, being washed away by the water from the shower above them.

Before he could do anything her hand shot out and grabbed his balls, hard, shocking him and making him wince in pain.

"Shit! Grayfia! It's hurt!" To make it even worse, her other hand moved to his cock and stroked it as fast as he could. A mixture of pain and pleasure would definitely turn him on, but the pain was a bit too much for him to handle.

"Let's me guess… Serafall teased you the entire meeting, didn't she?" Grayfia asked with a sadistic smile, tightening the grip on his cock even more "That bitch doesn't know when and where she shouldn't lay my hand on my husband, does she?"

"Ouch… let…" The pain disappeared as soon as Grayfia released his testicles and turned into pleasure when Grayfia got down to her knees before him and took his cock into her mouth, sucking as hard as she could while wrapping her tongue around the part inside of her mouth.

"Well, it's actually my fault, I should have come with you." Grayfia pulled back with a wet pop and traced her lips on the length.

"Eh… it's alright." Issei laughed nervously, sighing in relief after realizing that she wasn't that mad at him.

As Grayfia kneeled there, popping her head on his cock with her hands gently fondling his balls, Issei started washing himself and when he was done, Issei washed Grayfia's hair for her while still in the same position before he picked her up and gave his wife one of her favorite baths, with his cock deep inside her ass and his hands roaming all over her body, scrubbing the soap on her perfect skin, paying extra attention to her giant breasts before turning on the shower again to wash the slippery body wash away while jackhammering his cock into her backdoor.

Too bad that they couldn't have sex that night because their son Millicas wanted to sleep with them, and when that happened, Tiamat and Kuroka couldn't join in either.

However, he was very eager to make up to all three of them the next morning.

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 ** _End of Chapter 3_**

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 ** _Yagami's note:_** **Yep, still peerage mayhem! Though, it's not as long as I hope, so I think 5k+ for this chapter should be okay. It's just that I had decided to drop the 300 Issei thing, because it's too much of a clinch, since it's going to be created much later in the future. Also after reading Omni-Creator Kami of Anime's review and giving a very sage thought about it, I couldn't help but agree with him and decided that Issei, the true and real Issei should be the one who take his lover, as they are rightfully belong to him.**

 **I hope you like the first two choice of his peerage, Tiamat and Kuroka, and the amount of pieces Issei used to turn them into his servant. In Tiamat case, usually it wouldn't take it less than a Queen piece to reincarnate the strongest dragon king, but I believe that Issei, with the power of a super devil and his sacred gear Boosted Gear, is way way more powerful than her. So a mutation Rook Piece should be enough. The same for Kuroka, one Bishop piece is enough to make her his servant**

 **So currently, his peerage is like this:**

 **Queen: Grayfia Lucifuge**

 **Knight: Unknown, Unknown.**

 **Bishop: Unknown, Kuroka.**

 **Rook: Unknown, Tiamat.**

 **Pawns: Unknown, Unknown, Unknown, Unknown, Unknown, Unknown, Unknown, Unknown.**

 **Familiar: Unknown…**

 **Unknown will be opened for suggestion. It can be characters from different series, or characters originally from cannon DxD, or even an OCesses that are logical enough to put her into this story. Since Issei dream is to have a peerage full of girls for his harem, I would like to keep it like that and will make it an entire group of girls. For the fun of it, his familiars can be the same as well, but she or they have to be animal-girls to be made into his familiar.**

 **Remember that this is porn with plot. Soon, the plot will come.**

 **Next chapter: The King of Harem.**

 **Another timeskip (this one, however, is huge) and Issei get to do something he has always wanted to do in his past life, even though he is going to have to commit a crime, which isn't that illegal in Devil's way of life.**

 **More peerage's members introduce, more sex scenes will be included.**

 **READ and REVIEW**

 **Ja ne!**


	4. The Harem King

_**Important notice: I don't want people to point out the kinds of sex I usually write on my stories, you have problem with them? Don't read! Because it's MY OWN writing style! Got it?! That's how I write and want to write! You can throw flames at the ideas or my… grammar as much as you want, because it's something that I can improve!**_

 _ **People have different tastes, so stop questioning!**_

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 **Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

* * *

 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one knows about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

 _ **Issei Lucifer: The Harem King**_

 _ **Chapter 4**_

 _ **The King of Harem**_

[ **Timeskip- 9 years later** ]

"Alright ladies… line up and take my cum." Issei Hyoudou announced loudly and abruptly pulled his dick out of his MILF of a wife's tight little pussy and stood up while jacking his cock furiously in his hand. The entire group of his lovers, including Grayfia lined up the way he wanted them, with their arms wrapped beneath their tits, pushing their huge racks upwards and their tongue stuck out of their wide open mouth. Issei then felt his balls tensed and within a second or two, groaned as he pointed his cock downwards.

Grayfia moaned in delight as the first thick ropes of cum erupted from his cock and splashed on her face, as it was so large that it ran from her face, down to her neck and pooled in her cleavage, coating her upper body in a huge mask of white sperm. The next load went across Kuroka's face and round tits, glazing them with a thick spread of jizz, making the mischievous cat girl meow out in delight at such a treat of milk from her master. Next, he aimed his cock at Tiamat, who was kneeling at Grayfia's left and unleashed a fountain of milky white jizz across her face, the pent-up torrent of cum covering her mounds, rolling down to her flat toned stomach through the valley of her breasts.

Issei gave the next few jizzs to another MILF, who kneeled behind Grayfia with her giant tits rest on his wife's head, giving him a very seductive, almost sickening sadistic smile. Said MILF was none other than Shuri Himejima, former lover of Vice Governor General of the Fallen Angel Baraqiel and Akeno's mother, who chose to become his servant, his Pawn to repay him after he saved her and her daughter from the people of her own clan. Issei didn't expect Shuri to fall in love with him a couple of months after both mother and daughter came to live with them, but in the end he couldn't refuse such a beautiful and attractive woman like her. The fact that she looked so much like her daughter made thing even more exciting for him.

The two of them usually engaged in SM acts together, and despite their status, he was usually be the one who got tied up and wiped around by his Pawns. It wasn't like he had any objection because it brought new thrill to his sex life, but as a dragon by nature he didn't want to get dominated by anyone, especially the female.

Let's just say that he brought an M out of an S, and sexually punished her senseless with his big dick.

Of course, Baraqiel wasn't happy with the fact that the leader of devil was screwing his former lover… and soon, his daughter.

The next woman who got her face and tits full of his cream, was yet another extremely voluptuous woman with the beauty far surpassed any other, rivaled only by the other ladies of his harem with long pink hair, green eyes and creamy white skin unlike her kind, Akasha Bloodriver. She was a powerful Shinso Vampire who nearly gave up her life to protect the world from Alucard, formerly known as Court Dracula before his kingdom was destroyed, who intended to destroy the world in seven days but was stopped by Issei and his peerage five years ago. Issei, with Grayfia at his side, single handedly defeated the giant creature that the first vampire had become, saving the world. The Vampire Factions, Carmilla and Tepes, were extremely grateful for his help and decided to marry Akasha to Issei, as his concubine in order to bring the two races together, despite the fact that she's already married to Issa Shuzen and had with him a daughter, who was nine year old at the time.

Of course those prideful vampires would do something like that because while one of the most powerful, Akasha wasn't a natural born vampire and their nature didn't allow them to accept such thing like that. Issei accepted her with open arms, and even though Maou wasn't allowed to have a harem (till that day, Issei still believed that it was a bullshit law) the higher-ups had also admitted that it was an opportunity too good to miss. An alliance with the vampire, one of the most powerful Youkai would make Devil a fearsome race to the other Factions. Akasha was also the leader of the legendary three dark lords, whose powers rivaled even the leader of Youkai Faction, the Kyuubi Yasaka herself.

It was a marriage on papers only, but Issei came to love Akasha just as much as he loved the other and the same could be said to the young Shinso Vampire. Issei decided to make her his Rook with a mutation evil piece a couple of months after their wedding, and she had been loyally serving at his side since then.

Last but not least, the one who took Issei his last Bishop to turn her into his servant was a woman that was called the most powerful magician the world had ever seen, Irene Belserion. Just like any women of his peerage, she was a very beautiful and extremely voluptuous young woman, with big breasts, wide hip, and beautiful scarlet hair that was thickly braided and located in the front and back of her body as pairs. Issei met her a few years back when he decided to make a new pact with magic user, and Irene became the one who he made a ten years contract with. One thing led to another and the next thing he knew, she was on her knees sucking his cock, and just like that became one of his many lovers before he decided to make her his servant.

Like Tiamat, she was given the title of strongest as soon as devil society learnt about it.

He couldn't help but grin like an idiot at the thought of how his life had turned out.

Again and again his cock lurched in his hand, delivering streams of sperm all over them, coating their faces and their tits in his dick juice, and the women could do nothing more than quickly lapping, scooping and sucking it up into their mouth, as he finally stopped after half an hour straight of nonstop cumming. Issei groaned when Kuroka reached out and pulled him closer, guiding his cock to her mouth where she sucked and licked it clean for him.

"You have done it again, darling." Grayfia giggled softly as she stood up and wrapped her arms around his neck, pressing her large breasts to his chest "I'm so disappointed in you right now, master." She then pressed her lips against his, kissing him passionately before leaning back so he could feast on her breasts, which had grown a cup bigger after she gave birth to their son, Millicas.

"It's morning already?" Akasha asked a lout as she looked at the clock before massaging her forehead when she was suddenly hit with a slight headache "He's really done it again." The pink haired vampire moaned, as sperm was steadily flowing out of her pussy and asshole, just like the others.

"Like a dragon, I suppose." Shuri giggled and licked his cum from the tips of her fingers, nudging Tiamat slightly and giving her a meaningful wink.

"Are you sure you didn't give him any aphrodisiac last night, Shuri? Because that sounds like something you would do to keep him go forever." Irene spoke up, wiping the last glob of sperm on her breasts, which were full of bite marks and put it into her mouth "Or… he's just that pervert."

"I don't know what about you girls but…" before Akasha could finish that speech, Issei grabbed her around the waist and put her on all four after managing to let go of Grayfia's breast, positioning his cock at her pussy entrance "Ise-sama, wait I'm still…Ah~" the Shinso vampire moaned out loudly when Issei thrust his cock in and started pounding away into her.

"Well, I don't think we're able to leave this place until that monster go down." Tiamat shrugged and the other soon joined in as well, eagering to tame the wild dragon with their own flesh.

To many men, it was like the wildest wet dream possible but to Issei Lucifer, formerly Issei Hyoudou of the old timeline, it was simply another morning.

 _ **Line Break**_

Around midday, after finishing his works, Issei decided to take a trip to the human world with Grayfia. His parents, as well as his relatives, didn't exist in the new timeline, but Issei still came to the empty lot that used to be his house time to time to remind him about them, making sure that they would never be forgotten, at least by him. Grayfia would always find herself getting curious about the place every time she came there with her husband, but chose not to question her husband because she respected his privacy more than anyone and for that, he was very grateful.

After that, the two made their way to Kuoh Academy. It was Saturday, so there was no one at school at the moment. Looking at the old school building from the other side of the gate, Issei couldn't help but smile fondly at the memories. Before becoming a devil and Rias' servant, Issei thought there was nothing special about the school, other than the fact that it was originally an all-girls private school, a perfect place for pervert and horny teenager boys like him to enjoy the greatest times of their life. Soon, Issei realized that there was nothing but special about Kuoh, because the school had become the target for many evil forces around the supernatural world, Kokabiel and Khaos Bridage to name a few. Even the meeting between the leaders of three Great Factions from the Bible was also held there.

It's too bad that he would never be able to attend the place as a student ever again.

"Where are you going, Issei-sama?" Grayfia asked suspiciously while looking at him with half-lifted eyes, because she got a feeling that she knew where he was heading.

"I want to pay Shuri and her daughter a visit. Why? Is there anything wrong with that?" he smirked slyly and returned Grayfia's question with his own. The beautiful silver haired Queen looked at him for a moment before sighing in disappointment. She should have seen that coming from him, because after all, she spent the last fifty years trying to keep him from sneaking away, abandoning works to fuck some random women he found attractive enough to suck his glory cock.

"Oh no, no you don't Ise-sama." Grayfia raised her hand and stopped him "You're not going anywhere, not until you finish the rest of your works." She pointed out while giving him a stern glare "It's time to go back."

"You're no fun at all Grayfia." Issei pouted "How about this, I…"

"Do not try to bribe me, Ise-sama." Grayfia shook her head, hardening her glare "Sex with you is not that…" but before she could say anything more. Issei grabbed her around the waist and shot into a nearby alley before getting to work on his own clothes as well as Grayfia's clothes. In a blink of an eye, Grayfia realized she was pinned against the alley wall, maid-uniform loosened, bra removed and thrown to the ground, her huge tits on display, legs spread, and panties pushed down to her knees. Issei had one hand holding her wrists together above her head, his knees made sure she couldn't kick or knee him in the sin, keeping her firm against the wall. As much as Grayfia didn't want to admit it, Issei could easily overpower her and stop her from beating him up like usual, it was just a matter of want or didn't want to do it.

"Ise-sama…" Grayfia gasped when her husband/master raised his hand and smashed her tits, hard.

"Excuse me?" Issei asked with a sly smirk "But were you trying to say sex with me wasn't that good?" he lowered his hand to his pants and unzipped the zipper of his pants, making Grayfia's eyes widen in realization.

"I-Ise-sama… we can't… not here, we're in public." Grayfia said nervous "What if someone sees us?" but it was too late, his cock was out of his pants. Issei grinned and stroked his dick as fast as he could, forcing it to get hard as fast as possible while keeping his eyes on Grayfia's erotic body.

"Don't worry, no one will see us." Issei grinned "But they might hear us, so better keep your voice down, okay?" He asked sweetly, making Grayfia smile forcefully and try to free herself by struggling "Oh no, you don't Grayfia, you're not going anywhere, not until I'm done reminding you how great sex with me is?"

"I-Ise-sama… I was just kidding." Grayfia tried to talk him out of it while Issei was rubbing his massive cock-head against her rapidly moistening pussy lips "I was just trying to convince you to…"

"Too late love." Issei gritted his teeth and grabbed her waist, making a wide smirk and spearing his dick into her pussy, forcing the bulbous tip of his cock into her womb in one single thrust "Better hold on tight Grayfia, because I'm going to take you to a wild trip." Pulling out half way, Issei then delivered a sharp fast thrust back into his beautiful wife's tight little pussy, developing a rhythm of fast, hard thrusts that forced Grayfia to cover her mouth to stop herself from loudly crying out in pleasure, while her arms came up to wrap tightly around his upper torso and her legs wrapped around his thigh, her chin rested on his shoulder.

 _Line Break_

 _ **Ding dong!**_

After he settled things down with Grayfia and sent her home, Issei headed to Shuri's house, which located right next to the shrine Akeno used to live in in the old timeline, and pressed the doorbell as soon as he was there, as he could hardly wait to play the dominating game with the sadistic woman.

However, the one who answered the door wasn't Shuri, but a beautiful young woman with a voluptuous figure around the same age as Rias, her face greatly resembled his [Pawn], with very long black hair and violet eyes. Her hair was tied in a long ponytail, reaching all the way down to her legs with two strands sticking out from the top and sloping backwards, with an orange ribbon keeping it in place. Like the first one, she wore the customary Kuoh Academy school uniform for girl, along with black knee-high socks. She was none other than Akeno Himejima, Shuri's daughter with Baraqiel and his sister's Queen.

And from the small apron she was wearing around her waist, he could tell that Akeno was working in the kitchen before leaving to answer the door.

"Ara, Lucifer-sama." Akeno gasped in surprise and bowed her head at him, her hands put together on her lap "Welcome, to what do I owe this honor?"

"I'm here for your mother, Akeno." Issei smiled before tiptoeing over to look into the house, searching for another black haired Himejima "Is she at home?"

"Well, my mother went to buy groceries at a nearby shopping mall." Akeno told him "So it's up to me to… keep you company if you decide to wait." She said, smiling seductively. Her words made Issei to look at her giant breasts, which were probably one of the the biggest pairs of tits around, and it didn't go unnoticed by Akeno.

Akeno, meanwhile, had become even more obsessed with Issei after he rescued her and her mother. Much like Rias, for the past few years Akeno had been staring at him with nothing but lust in her eyes, acting like a horny high-school girl whenever he was around or came to her house to 'visit' Shuri. In the old timeline, despite being seductive and quite flirtatious toward him and acting like a mature young woman, Akeno was still innocent and emotional towards love; however, in the new timeline, with her mother around to guide and teach her, plus Issei's constant visit to their house, Akeno had become quite mature and bold in said aspect.

Ophis had stated very clearly that even though she resetted the timeline, she decided to keep Rias and the girls' feeling for him intact, because it would be very difficult for them to fall in love with him again without him there for them like the last time. Maybe he could manage to pull it off one way or another, but Ophis believed it would be better that way.

Of course, she wasn't unfamiliar with the story of Issei Lucifer and his unrivalled sexual prowess, Akeno being the first low-class devil who knew about it from her mother. Hell, he could even feel her eyes on his back whenever he decided to have his way with Shuri in her house.

"Great." Akeno stepped out of the way and let Issei to walk into her house "So… exactly what do you need my mother for, Lucifer-sama?" She didn't need to hear it from him to know the answer, because there was only one reason for him to be there, at her house.

"Well, I need your mother to do some improper things to me, Akeno, as well as the other way around." He said, acting like he was serious.

"Ara ara, are you sure it's legal for you, a Maou, to do that, Lucifer-sama?" Akeno gasped in surprise and shock, but like him, she was acting "Having improper relationship with someone not your wife?" He knew that Grayfia was Akeno's idol, because she was a big fan to their love-story, just like the original timeline.

"Don't worry, nothing I can't handle." He turned around and smiled at her "Also, call me Issei, you don't have to address me so respectfully like that when we're alone. After all, we're all family, aren't we?" he walked into the living room and took his seat on the longue.

"Yes we're, Issei-sama, yes we're." Akeno smiled before continuing "Please wait here, Issei-sama. I will make you some tea" Issei nodded his head in approval, allowing Akeno to head back into the kitchen to make tea for him. However, because he was facing away, he couldn't see the smirk on Akeno's face when she turned around and walked away ' _Sorry Rias,'_ She thought, her hands reaching for the buttons of her shirt ' _But it seems… I'm the lucky one.'_

Issei didn't have to wait long, though "Here is your tea, Issei-sama."

"Thank you Ake… woah!" Issei made a sound in amazement when he saw his sister's Queen, standing before him wearing absolutely nothing but the pink apron, which ended just below her pussy and left a lot of cleavage, the sides of her breasts, as well as her entire behind completely exposed. The sight of her voluptuous body, hiding behind nothing but a small apron like that, made him want nothing more than bending her over and fucking her as hard as he could "Girl, you sure know how to please your superior, just like your slutty mother?"

"Ufufu, I'm glad that you like it, Issei-sama." Akeno giggled and bended over, with her hands on his knees to kiss him on the lips when Issei made a 'come here' gesture with his index finger. Issei sat there and parted his lips slightly, allowing Akeno to insert her tongue into his mouth. They made out for a full minute before Akeno pulled back, thin a thin trail of saliva connecting the tip of their tongue together.

"Quite a talented mouth you have there, my dear." As he spoke his hand cupped her breast, squeezing it delightfully, twisting her nipples between his fingers through the thin material of her apron, making Akeno become hornier than ever "How about you put it into good use while I enjoy your delicious tea?" Issei released her breast and leaned back against the backrest, holding a cup of tea in his hand.

"With pleasure, Issei-sama." Kneeling down between his legs, Akeno swiftly had his bottom half naked, before staring in awe at the man meat in front of her. She watched her mother getting fucked by her master multi times before, but it was the first time Akeno was able to see it so close like that, and realized his cock was a lot bigger than she thought, and he was still soft. Akeno then wrapped on hand around the base, but her hand couldn't come close to encircling it. She started to slowly jerk him with both hands, feeling it swell until she could barely wrap two hands around him. She gaped in bewilderment; it must be over fifteen inches long and extremely thick as well.

As she paused to admire it, she felt Issei's hand on her head, pushing her towards his pole while he was still enjoying Akeno's delicious handmade tea. The black haired Queen eagerly leaned towards him, sucking on the tip as it pushed into her mouth. She drooled at the taste and realized that she could suck his cock all day! She quickly sucked his whole head inside her mouth while pumping the rest of the cock with her hands, drawing a moan from the powerful super devil. She swirled her tongue around his head, licking up the pre-cum spilling from his tip, eagerly using her hands to serve Issei's large balls.

"Surely you can do better than that, Akeno dear." Akeno gasped and had to fight back the urge to gag when Issei, using his grip on her head, forcefully forced his dick down her throat, finding her lips locked nearly at the base, and his head poking her stomach. Sighing in pleasure, Issei kept her head like that for a moment and slowly poured the hot tea down her naked back. It wasn't hot enough to burn her, but it hurt her enough to bring out her masochism nature. As the hot liquid running down her curvy back to her ass crack, Akeno arched her back and moaned out lustfully, causing her throat to vibrate around his cock. Issei then started to fuck her face onto his cock and she responded eagerly, sucking as hard and licking as much of his cock as she could.

His heavy balls, which, like his big cock, were covered in saliva from her stuffed mouth, clenched and she felt her treat empty into her throat. His first shot filled her mouth completely, some flowing straight to her stomach. She swallowed his thick delicious cum as quickly as she could, trying to get it all. Despite her best efforts, some spilled out of her mouth and fell onto the top of her tits and the chest area of her apron.

"Like mother, like daughter I guess" Issei chuckled as he finished the last of his tea while watching Akeno doing the same to her first ever treat of his sperm. As Issei finally stopped cumming, his grip on Akeno loosened, allowing her to back of his still hard cock.

"Did I do well, Issei-sama?" Akeno asked, planting a wet and loving kiss on the tip of his cock

"You did well, Akeno" The Maou grinned then stood up, removed his shirt, and Akeno found herself drooling at his impressive abdominal muscles which looked like stones stacked up to his chest "But it's time for me to enjoy the main course." Akeno almost creamed herself at the thought of what about to come.

"Do whatever you want, Issei-sama."

Smirking slyly, Issei grabbed her at the back of her neck and roughly bent her over the table with his still hard cock kissing the entrance of her pussy. Then with a manly grunt he shoved in, thrusting twelve inches of his cock balls-deep without any gentleness, breaking her hymen before she knew it, and when his cockhead slammed into her womb she let out a deep, satisfied scream.

"Well, shouldn't expect anything less from the daughter of a slut, should I?" Issei grinned, taking a hold of her hip with both hands and started to fuck her with his cock, working the last few inches into her cunt before going wild with her tight, virgin pussy. He pulled out and slammed back in with long, hard thrusts, slamming his hip against her ass again and again and again, his rock-hard hips practically spanking her inner-thighs. Akeno was quickly cumming her brains out, and her hips bucked as waves of pleasure ripped through her body.

It didn't take her long to cream her inside with his sperm. For several long moments, Issei remained inside her, moaning into her ear as his orgasm waned, the shear amount of semen Issei Lucifer was pumping into her womb after the first few minutes caused her abdomen to expand as if she were already nine months pregnant.

Her cunt desperately clutched at his massive invading shaft, his final thrusts making her cum again and again and again. Then he stepped back and pulled his enormous cock out of her slowly, inch by inch until only the head of the fifteen inch shaft remained within her fertilized cunt. Finally he ripped the head from her pussy and stood aside. A torrent of pressurized jizz spurted from the black haired Queen's gaping cunt, splattering the opposite wall. Akeno moaned as she began to deflate, blasting cum all over the floor. Finally the torrent slowed down, Akeno fell and sat on the ground with her back lean against the table, breathing heavily, utterly spent.

"The fuck are Shuri doing?" Issei wondered while looking at the clock "Oh well." The brown haired boy shrugged and turned back to Akeno, who had regained her composure and smiled at Issei, who were staring at her breasts and thinking about the best way for him to enjoy the largest pair of tits around.

Little did he know that Shuri had returned long before Akeno started sucking his cock, but chose to leave quietly after realizing her daughter's intention and couldn't stopped herself from silently cheering for her daughter, imaging about a possible threesome between the three of them.

* * *

 _ **End of Chapter 4**_

* * *

 _ **Yagami's note: Well! Have to end this chapter like that. This chapter was supposed to be Issei's time with Rias, but I couldn't find any ways or any opportunities or any special situation for Issei to approach Rias and then turn her on enough for him to fuck her. It's really, really hard you know! I have decided to end this chapter midway like that to announce this:**_

 _ **So, I will let you bros decided it. Give me your thoughts about how Issei should approach Rias, logic enough for sex to happen afterward. The most logical way I find will be used for this story, because everything I had come up with is too illogical to be used.**_

 _ **This chapter also introduced the new members of Issei's peerage/harem, who he's going to spend a great deal of time with in the next and future chapters. Irene Belserion from Fairy Tail, because I has come to like her a lot and she will be a great addition to his harem as a Bishop. Shuri Himejima as his Pawn and Akasha Bloodriver as his Rook, since many reviewers had requested these two.**_

 _ **With the background I set up for Akasha, this story is officially linked with Rosario Vampire (*evil laughter*).**_

 _ **Next chapter: Mother/Daughter combo**_

 _ **READ and REVIEW**_

 _ **Ja ne!**_


	5. Family matter

**Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

* * *

 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one knows about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

* * *

 **Note: The first half of his chapter is based on the fifth chapter of tempfile's Zeus, Lord of Goddess and Demigoddesses. I have added my touches, but all credits go to him. I was having a very bad day while writing that part (The corner of my cellphone fell onto my toe, causing me to step onto dog's shit.) so I asked tempfile to lend me the scene so I can get the part over with and cool down.**

* * *

 _ **Issei Lucifer: The Harem King**_

 _ **Chapter 5**_

 _ **Family matter**_

Akeno Himejima, the busty queen of Rias Gremory, was having a very wet dream, a dream that was filled with beautiful women worshipping a certain cock, and she found herself among them, madly fingering her pussy as she waited for her turn beside Grayfia, the strongest silver queen of the underworld, who was slurping on the massive meat that extended from her husband's groin. It was at that moment she noticed she was the only one who was wearing a slave collar and the chain were being held by Issei. Simply put, she loved it.

As Grayfia pulled back and released his cock from her mouth, she moved to the side and let Akeno take her position. When she was about to swallow her master's dick down her throat, she woke suddenly, disappointed at the denial of her prize.

When she woke, she was greeted by the incredible feeling of pleasure of having his fingers working their magic inside her cunt while stroking her clit expertly at the same time. Her eyes crossed as she came for him, writhing on the bed in ecstasy. As she came down from her high, she noticed the newcomer in her room. On her knees with her ludicrously large boobs wrapped around the even bigger dick she was worshipping, was her mother. "Kaa-san?" She asked, blinking several times to clear her vision

The beautiful black haired woman looked at her daughter and gave her a wink "Good morning, Akeno-chan. Did you have a nice sleep?" She asked sweetly, and Akeno nodded her head "Well, when Ise-sama was done with you, I noticed he wasn't completely satisfied. I couldn't just ignore such a painful erection from my master, so I decided to come in and accept his divine treat!" She punctuated her words by giving Issei' cock a nice long lick, making him moan in satisfaction "Especially with your delicious cum all over it." She gave Akeno a wink then went back to servicing Issei.

"I passed out, Issei-sama?" Akeno asked, looking at her new master.

"Yep, you passed out after I came inside you three times." Issei said with a grin "Not bad for a first timer, but I hope you have recovered, because I'll need you to come here and help your mother." The brown haired Maou said, his fingers ghosting over her still sensitive clit "Or I will have you punished." He said sternly, and then smacked her gushing cunt roughly, eliciting a pleasure cry from the young fallen angel, who then crawled over to her mother, getting a solid grope in before going to work on Issei's heavy balls while her mother's tits and mouth covered the rest of his manhood.

Issei watched as the mother daughter team took turns stuffing his dick down their throats, each encouraging the other to get deeper, and sucking on each other's tits as they went.

"This is the best." Issei said blissfully as he leaned his head back against the pillows when Akeno and Shuri started making out with each other around the tip of his cock while having their breasts wrapped tightly around his cock. Being the one with a bigger pair of tits, Akeno was having an advantaged against her mother, but since she had much more experience with his giant dick, it didn't take Shuri long to equal their games. As soon as their lips were separated, the black haired mother and daughter grabbed as much tits-fleshes they could hold in their hand and started wildly pumping their breasts up and down his length. The loud, rapid slapping of their breasts against his thighs filled the room and along with the moaning, were the only sounds they could hear.

"That's it, I'm cumming!" Despite his best efforts, the wonderful experience became too much for his brain to handle. The Himejima didn't have to wait long as Issei groaned loudly and shamelessly, jerking his hip upwards and came, spewing his first load into the air with such force it managed to reach several feet in the air, nearly hitting the ceiling before splattering down on his daughters like gooey rain. Akeno and Shuri watched in awe and moaned in delight as sperm fell down their faces, their heads and their breasts and splattered all over their bodies.

He came for god knows how long. When the flow of cum finally died down, he could finally moan happily and watch his lovers cleaning his cum from each other's body using only their tongues. It was truly a sight to behold when they licked their faces and breasts clean from his cum. They drank a lot, but still kept a decent amount of cum in their mouth to give each other when they kissed again. Such a sight only made his cock become harder than ever.

Unable to take it anymore, he grabbed Shuri by her armpits and threw her onto the bed, tits up.

Not pausing for a moment, he got on top of her and slammed himself into her soaking wet core, splitting her open as he speared his cock into her womb. Shuri Hiemjima's world went white as she came everywhere, squirting all over her King's cock as it stretched her to the limit. "Fuck me, fuck me fuck me, Fuck me till I break!" she cried, delirious with pleasure as she got the pounding she had always wanted from her master.

"You turn a sadistic woman into a masochist slut, as expected from you master." Akeno said and decided to shut her mother up, lying on top of her while she was mercilessly pounded and shoved her big right tit into her mother's mouth who moaned as her mother suckled at her nipple, bringing the slutty fallen angle over the edge quickly. "Kaa-sama, you're so good at that! Not even Rias can make me cum that fast!" Issei couldn't help but raise an eyebrow as Shuri continued to quiver on his thick manhood.

"Rias?" Issei asked, slapping Akeno's butt to gain her attention.

"You will be surprised to know what we do in our free time, Issei-sama." Akeno said with a seductive smile as she looked behind her shoulder "You should join us."

"Akeno, are you asking me to fuck my sister?" He asked, spanking her ass again before backhanding the other ass cheek, making Akeno moan in pleasure.

"Rias might now show it, but she fancies you." Akeno replied between moans "Plus, you don't have any problem with that, do you?" Issei didn't answer her question, he simply lifted Shuri's legs up, holding them by the ankles, and fucked her even harder, making her cum rapidly around his cock. Issei continued like that for twenty minutes, before he finally gave in the pleasure and delivered exactly what she wanted, filling her to the brim with his thick, hot seed.

After he was done cumming, Issei pulled his cock out of her cunt and sat back, deciding to take a breather from the marathon of fucking.

"Akeno, come over here and clean my cock with that pretty mouth of yours." Issei ordered after slapping her ass.

"Of course, Issei-sama." The slutty daughter of his pawn obediently crawled on all fours over to her new master's open legs, where she gave his cock a long, wet and loving lick before she launched herself at his stiffed cock, stuffing it down her throat and sucking her mother's cum off of it at the same time. Calming down from her high, Shuri pushed herself up to see her lovely daughter pumping her eager mouth up and down Issei's huge shaft while her hands lovingly caressed his cum filled balls.

"You sure know how to work that cock, slut." he groaned, pushing her head down even further as she choked and sputtered around his tree trunk of a cock before looking at her mother "Shuri, lube her ass for me. I'm going to take her ass' virginity next."

"Will do, master." Shuri lowered her head submissively before she parted her firm ass cheeks and shoved her tongue right into her bowels, starting to eat out her virgin ass. Relentlessly pumping her throat on his cock, Akeno then stopped and pulled her back slowly, sucking along the way before releasing the tip from her mouth in a wet pop.

"You're going to fuck my ass next?" she asked, looking up at him innocently.

"That's right, and I'm going to mark it as mine, just like I did to your mother." Issei grinned in response and reached down and tweaking Akeno's nipples, drawing a half-yelp half-moan from the girl.

"Do as you please, master." Akeno said, before reaching her hand behind her to remove her mother's head from her ass. She knew exactly what to do, and turned around quickly, getting on all fours and presenting her well-lubricated ass to the leader of the Devil Faction. Shuri smiled, and sat beside her daughter, her hands cupped her ass cheeks and spread them, showing Issei the place where his cock would settle in next.

"Take her like you took me, master." Shuri smiled and Akeno wiggled her ass enticingly. Without further ado, Issei stood behind and teased the fat dip of his cock against her asshole "Also, you don't need to hold back. She loves pain."

"I know."Issei smirked and slammed right into Akeno's virgin ass.

"Oh fuck!" Akeno cried out as she came from the pain, and pleasure of having her ass penetrated ruthlessly like that. She could feel her asshole rearranging for the enormous invader and she loved it. Grabbing her womanly hips, Issei pulled his back and then plunged forward, adding two more inches as he settled half of his cock inside her ass. Without giving her time to recover from the latest mind-blowing orgasm, Issei repeated the process and managed to go even deeper into ass, sending her over the edge as his heavy balls slapped right into her hypersensitive clit. Issei smirked widely as he felt Akeno's ass writhing around the part of his cock he could inside unbelievably tight ass.

Picking up the pace, Issei fucked Akeno's ass for what felt like hour, his cock plunged deep and hard against her backdoor, causing Akeno to squirt and cum her brain out. Even he was Issei Hyoudou he had dreamed of the day that he would take Akeno like a slut and give her just what she wanted, but now that she was on all four in front of him with his cock deep in her ass, he must admit it was nothing he had imagined. It was mind-blowing and he loved every second of it.

Time passed, and it's nearly morning, Issei had reached his limits but was doing everything he could to savor the feeling. His hips turned into a blur as his cock disappeared and reappeared from Akeno's ass faster than the normal eyes could follow. They both knew that she wouldn't be able to sit straight without a proper medical treatment, like a healing spell, but it definitely worth it.

Then, with a dragon-like roar, he unloaded inside Akeno's ass, filling it to the brim. He came like that for minutes, painting her inside white before pulling out and settling it straight down Shuri's equally tight throat. Instinctually, she swallowed his' potent seed without missing a beat.

"Let's call it a day with a round of BDSM, shall we?" Issei looked at Shuri, who still had his cock stuffed deep in her mouth, and suggested with a smile, causing the eyes of the black haired woman to shine in excitement.

Line Break

"Honey! I'm home!" When he walked into his office, Issei announced his return loudly and cheerfully, causing Grayfia who was cleaning his desk with a white cloth to look at him strangely. He didn't return that night, and even while standing fifteen feet away from him, she could smell feminine perfume on his body, but it wasn't anything new to her.

"Good morning, Issei-sama." Nonetheless, she stood up and bowed her head to him respectfully "I hope you have had a wonderful… what are you doing?" She asked sternly and was formed to move her head back to dodge his lips when he wrapped his arms around her back and tried to kiss her.

"Aw, you're no fun at all Grayfia." He said, grinning at her.

"I don't think I quite understand what you want to say, Issei-sama." Grayfia questioned with half-lifted eyes, unamused.

"Grayfia, Grayfia…" his second wife, Akasha Bloodriver elegantly walked in with a smile on her face "you're supposed to kiss your husband to welcome him back. Like this." When she was right next to him, Akasha put her hand under his chin and gently turned his head toward her to kiss him. She kissed him passionately, but made sure to leave enough space between lips for Grayfia to see their tongue entangling with each other. The silver haired queen said nothing, but she did click her tongue in displeasure "Welcome back, dear." She said after pulling back.

"Now that is what I am talking about." Issei said, pointing at Akasha who smiled and lovingly rested her head on his shoulder "You should try it sometimes, Grayfia."

"I will, when my shift is over." Grayfia answered stoically "Where were you last night, Issei-sama?" Before he could say anything to answer her question, Akasha leaned over and inhaled slightly to take in his scent.

"Ah, you spent the night at Shuri's place, didn't you?" She asked before taking another inhalation "Hm, there's another smell quite similar to Shuri's scent here… did you fuck her daughter?" She asked loudly, sounding surprised but in truth, she wasn't.

"Yes, I did." Issei nodded his head and answered while chuckling nervously, looking at Grayfia who was openly glaring at him.

"I'm not surprised but try to control yourself next time, dear, or else there won't be any women left for other men out there." Akasha giggled and kissed his cheek again "Can I have my dinner and breakfast please. I didn't get to drink your blood last night so…"

"Go ahead then." Issei chuckled and let Akasha sink her fangs into his neck, drinking his blood while wrapping her arms around his chest."Grayfia, do I have any appointment today?"

"I believe you do, Issei-sama." Grayfia nodded her head and made her way toward his table, where she opened one of the drawers and took out a small paper.

"Oh, nearly forget to tell you…" Akasha said after releasing her fangs from his neck and licking the wounds, making it close and stopping the blood from flowing "Venelana-sama is here to see you." Issei's eyes immediately brightened up at the mention of his mother, or Rias' mother "She's expecting you in your room."

"Okay then. Shouldn't keep her waiting, don't you agree?" Issei laughed awkwardly and turned around to leave his office, missing the disappointed sigh of Grayfia and a giggle from Akasha.

"He really doesn't know where to stop, does he?" The silver queen asked while shaking her head.

"What can you do? Cock blocking him?" Akasha said, looking at Grayfia.

"He should just focus on me."

"Aw, jealous, aren't you?" Akasha giggled as she leaned her head on the maid's shoulder and wrapped her arms around her body, causing Grayfia to give her a stern glare "But I thought you had realized it by now that you cannot handle him alone. Me, as his second wife and his peerage are just here to make the night more pleasant to you. You don't want him to fuck you unconscious everytime you two spend on your bed, do you?"

"Still, it would be wise if he slowed down a little." Grayfia said, shaking her head "Also, what was Venelana-sama thinking anyway? It's okay to do that in our society, but…"

 _Line Break_

Opening the door of his room, Issei walked in with a rather lecherous smile on his face and then closed it behind him. There was a woman with brown hair sitting on his bed, watching a porno movie on the huge flat scene tv at the other side of his room. Said movie was simply a recorded footage of one of Issei's nightly sessions with his wife and peerage. It was recorded by Kuroka, who thought it was a good idea, and similar tapes like that could be found in his bedroom, being hidden inside a box that could only be opened by those he trusted.

"You have been busy." Venelana Gremory, formerly Venelana Bael, the Lady of the Gremory Household, turned her head around and greeted her son with a small smile "Good evening, Ise." Issei smiled back. Venelana looked just as beautiful as he remembered her in the past timeline. She looked exactly like Rias, with shorter brown hair and purple coloured eyes. She was wearing a dress that showed a lot of cleavage, which was his favorite.

"It's good to see you again, mother." Issei smiled and kissed her cheeks lovingly before pulling back to kiss her on the lips, like a man kissing his woman. Venelana happily returned the favour, as she moved his lips in sync against his before parting them and giving his tongue access into her mouth, moaning slightly as Issei skillfully put her tongue into good use "What did he do this time?"

"Do I need a reason to come and see my beloved son?" Venelana smiled teasingly as she grabbed him by his collar "And don't tell me that you don't want to see your mother." With that, she pulled his face toward her and let him push her down to the bed before attacking her neck, smiling blissfully when his hands went for her boobs while her right hand moved into his pants and found his cock.

If the memory of the other half didn't fail him, then it happened three years ago. Venelana angrily came to his place in a stormy night because her husband, the one who he now called his father, Zeoticus Gremory had neglected her for the women of his harem for a week straight. He spent his time having sex with them and ignoring Venelana's needs, and while he was a devil, he didn't have the stamina to keep up with all of them and usually passed out before the night could end, leaving a few of them unsatisfied and unfortunately his legal wife was one of them.

Issei tried to comfort his mother, and one thing led to another, the next morning he woke up on top of his mother's naked body. She had a very pleased smile on her face as she slept and her entire body was covered from head to toe in his sperm, hot and thick sperm, which explained that they had had sex all night till morning and only slept for a few hours before going at it again. After that day, whenever she was unhappy about her marriage with the head of the Gremory House, she came to his side to get exactly what she wanted, being held by a realm man and a good fuck from a big hard dick. Since incest was illegal in the devil society, as old tradition high-class devils of the same household usually married each other to keep their bloodlines pure, Venelana had no problem letting her son fuck her, and Issei Lucifer had no problem hammering his mother's holes. Now that Issei Hyoudou's personal and soul had been added, it was a lot easier for him to have sex with Venelana, who came to him every time she had the chances.

Of course, Grayfia and the others were fully aware of this, as Venelana had joined them on some special occasions.

Issei pulled back from Venelana's cleavage and as she continued to stroke his cock, his hands went behind her and found the zipper of her dress. Smiling, the brown haired Maou pulled the zipper down and grabbed the dress before standing up to remove it from her body. Venelana followed and raised her arms so he could remove her clothes in one single move, smiling seductively when she was naked, save for her arm-length gloves and thigh-high stockings, in front of him.

"Shall we do this, Maou-sama?" the brown haired woman asked seductively and reached her hands out for his shirt. She unbuttoned it down and removed his from his body, licking her lips at the sight of his muscular chest and torso.

"How was father?" Issei asked as Venelana removed his pants and held his cock with one hand while the other pushed his last piece of clothing down to his ankles.

"You know the usual." Venelana shrugged "Spending time fooling around with the others, neglecting me and my need… not every man can go forever like you, Ise." She sat down on the bed and brought out her tongue to lick his cock, causing it to jerk and harden just a little.

"Father must be a food to ignore a woman like you. You should be the one who he has sex with first."

"Aw, my son is so nice." Venelana giggled as she pumped his cock with both hands "Speaking of first, how was Grayfia? Was she giving it hard for you?"

"Nah, she can be jealous from time to time, but I make sure to spend as much time with her as possible, since she's my wife and the woman I love." He then quickly added "Not that I don't love the others, it's just Grayfia is more special."

"The two of you went through a war to be with each other, I can understand." Venelana smiled "I kind of envy her, having your husband paying so much attention to her like that. I bet that she has a generous share of you every night, doesn't she?" with that, Venelana parted her lips and took the head of his cock into her mouth, sucking it lightly while stroking the length with her hands.

"And every morning, depend on my mood." Issei said with a lecherous grin, leaning his head back and moaning in pleasure when Venelana tried to push her tongue into his cumslit "I think she loves spending the majority her time under my table and having her head between my legs while I am working."

"You know, maybe I should join her. Isn't your table big enough for two?"

"For three, actually." Issei chuckled as he put his hand on the top of her head, running his fingers through her smooth hair "How is Rias?"

"She's doing well, but still refusing to find a suitor or at least a boyfriend." Venelana said as she spit on his cock and started licking it with her tongue, lubing his manhood with her saliva.

"Who know, maybe it's because she's in love with me she doesn't want to be with anyone." Issei joked, which was actually not a joke. It was the truth. Rias' feelings for him were still with her so she must be in love with him and felt the need to be with him. Akeno's words to him about Rias last night confirmed that.

"Maybe, maybe not…" Venelana shrugged as she held his rock hard cock in hand "After all, the only man she has shown so much of a loving gesture is you. You should talk to her sometime Ise, she asked about you a lot in our dinner."

"I will." Issei nodded before saying while pushing his cock against her lips "Now, wrap those pretty lips around my cock and show me why I should waste my morning with you."

"With pleasure." She said and without a second thought, she took his cock into her mouth and begun to suck three inches of his cock madly. Issei watched as his mother, or in better word his new biological mother's lips stretched around the girth of his cock as she popped her head back and forth on his length, taking in another inch every time she shot her head forward while simultaneously licking her tongue around his cock, coating it in a thick layer of her saliva. With his hold on her head, Issei started bucking his hip, groaning in pleasure as his cock went deeper and deeper down Venelana's tight throat. While she was drop dead gorgeous She didn't have the tightest body he had ever fucked, that honor belonged to Serafall of course, but her experience definitely made up for it.

Pulling her head back and releasing his cock from her lips' tight grip, causing it to swing upward, Venelana leaned forward and pressed her face against his cock, breathing hotly as she pushed her lips and kissed his cum filled sack. As she stroked his cock with one hand, the other reached out and cupped his balls "There's so much cum inside." She said as she gently massaged them.

"And I'm going to dump them all inside you, mother." Issei said slyly as he rubbed his cock against her face.

"I can't wait." With that, she went back to sucking his cock, moving her head to the side before pushing forward until his fifteen inches manhood had rested inside her oral carven and her lips wrapped tightly around the base of his cock. Keeping her head like that for five seconds, Venelana then pulled her head back, sucking as hard as she could while trailing her tongue at the underside of his cock, slurping lewdly using the inside of her cheek. She repeated the process rapidly for the next fifteen minutes, increasing the pace with each passing second until she was madly slamming her head up and down his cock, sucking him a way that made him want to blow his load right there, but held back because he wanted to savor the pleasure of having her mouth around his cock. Issei felt his knees becoming weak when his cock throbbed and twitched with the need to explode with cum.

Unable to hold back, Issei decided to let it out and removed all kinds of control he had to fully feel the amazing mouth of Venelana before saying "I'm cumming, mother!" With that warning, Issei shuddered and flooded her oral carven with his sperm, causing her cheeks to bulge out and overflow at the sheer size of his first shot. She gulped down all as it came, not spilling a drop.

After ten minutes or so he felt his cock stop cumming before being released from Venelana's mouth.

"I can never get tired of the taste." Venelana commented as she licked her lips "Ready to give mother more?" She asked seductively. Instead of answering her question, Issei stepped forward and placed his cock between her breasts, pushing his mother back to get a more comfortable position before pressing those soft balls of fleshes together around his cock and started thrusting between them, the tips of his cock rubbed against her lips. He fucked her tits with no will control, and came ten minutes later, spraying his thick cum onto her face before feeding his load to her again.

"Man, this is some kinky shit right here." Issei commented as he pushed his mother's head down and forced her to deepthroat him for a full minute before pulling her head back to rub his saliva coated cock on her face "Now mother, I want you to lie down, spread your legs as far as possible so I can fuck that pretty pussy of you."

"As you wish, Lucifer-sama." Venelana lowered her head submissively and lied down, holding her legs by her thighs she then spread them as far as possible, giving her son full access to her dripping wet pussy.

Climbing onto the bed, Issei climbed onto his mother's body and pushed his cock into her cunt, causing her to moan in pleasure. Grinning, Issei pushed four more inches of his dick into her pussy and then pulled his hips back before slamming forward again, adding three more inches into his thrust, forcing Venelana to take over a foot long of his cock. Rocking her body with his strong thrusts, Issei caught her hands and put them together in front of her head, allowing him to have the full view of her bouncing breasts as he fucked his cock into her pussy.

"This is what you want, right?" Issei asked as he pounded his mother's pussy and womb with the full might of his cock "To be fucked by a big dick?! God! You're such a slut mother." He groaned when her pussy clenched tightly around his dick, making it hard for him to move but Issei had never failed to disappoint even in the most challenging condition "Take this! Take my cock!" He smirked and continued like that for the next hour, and by the time he was moving his hip in a blur, his hips slapping hers noisily as lewd and wet sounds were made, Venelana had lost herself to the pleasure and been moaning underneath him like a shameless slut. During that time, he was close to cumming twice but was able to hold back and continue giving his mother what she came to seek.

Eventually, he reached his maximum limit and thrust his cock as far up her womb as possible and cum, cum like a broken water hose, filling her inside up and forcing her belly to swell to contain his huge load. Several minutes passed as his cock remained still inside her pussy and Issei continued to unload his thick sperm into her rapidly expanding womb.

"So you look like this when you were pregnant with me?" Issei asked with a perverted grin as he looked at her swollen belly "No time to scoop my sperm out, turn around and show me your ass, Venelana." He said with authority, and Venelana could only obey him and do what she was told to do, turning around and getting on all four while raising her ass into the air.

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 **End of Chapter 5**

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 **It's been awhile folks. It's been awhile since I last updated this story, so I hope this chapter is worth the wait.**

 **Sorry I cannot write the chapter: The Fallen Archangel like I had promised. I had decided to save it for later and for a more suitable and special occasion. Issei will have his time with Gabriel later.**

 **Rias will join next chapter people! I have found out a way to add her into this story.**

 **Well, that's all I want to say.**

 **READ and REVIEW**

 **Also, if you're a fan of Kamen Rider, don't forget to check out my new story Kamen Rider Sekiryuutei, a crossover of Kamen Rider and DxD.**

 **All hail the lemon god!**

 **Ja ne!**


	6. Work and Sibling love

**Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.**

 **Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.**

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 **Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one knows about it, right? Issei/Harem. Warning: Hardcore and Incest.**

 **All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.**

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 _ **Issei Lucifer: The (secret) Playboy Lucifer**_

 _ **Chapter 6**_

 _ **Work and Sibling love**_

Sitting comfortably on the sofa in a high class hotel suite, Issei patiently waited for his client to arrive.

He was a Maou, one of the four leaders of the Devil Faction, so he didn't have to do Devil Jobs. However, they were something he had greatly enjoyed doing back then when he was younger, regardless of what they had been. In addition, his most favorite kind of work had been fulfilling sexual requests, because they had been his opportunities to have one-night-stand kind of sex with beautiful and attractive women without a care about later entanglements, as all that mattered were pleasure and satisfaction.

After he had become a Maou and married Grayfia, Issei didn't have much free time to answer these requests anymore, but recently he had his wife rearranged his schedule and had his Sunday's night completely free for them. Those old geezers on the top knew about this, but it wasn't like they could do anything to stop him from answering them. Women, devils or whatsoever, who were rich enough to afford his service were usually extremely powerful and politically had a lot of influences over their respective groups, so having Issei, one of their leaders, fulfilling their demands, sexual demands but still pretty much demands, could be a perfect opportunity for the devils to strike financial, political… deals with their factions.

Tonight was no exception, after having Grayfia and Kuroka going through the mountain of requests that had been sent from all over the world with him, Issei had chosen his ideal partner for tonight and contacted her to meet him at one of the fanciest hotels on the human world, near her house. Putting on something formal and pretty decent, Issei had headed there first, accepted his room for the night and waited for her to arrive. It shouldn't be long, because she promised she would be there by seven.

And she didn't disappoint him.

Hearing the doorbell, Issei stood up and went to open the door, coming face to face with the lady who was going to share a steamy hot night with him tonight. She was very beautiful, having the appearance of woman in her mid-twenties. She had light skin, long and wavy blue hair with purple eyes and large J cup breasts that daringly stood on her chest without a care about the law of gravity. She dressed to impress and to kill, with her outfit being a red, strapless dress that was also specifically a mini-dress in length, with black hem which barely covering her generous cleavage. Wore outside of her dress was a black coat with sparkles and blings with light tan fur on the collar. Her nails were polished red, and she also sported a pair of golden, made-of-gold heart-shaped earrings and a matching heart necklace, thin and small, to go with it. She also carried a small handbag with her.

Overall, she was a woman that men would kill to fuck. Her name was Ageha Kurono, a high class member of the Succubus race, the race of sex demons. He had always wanted to have a night with sex demon, directly. Having heard and read so much about them in his past life. Since his past self had already had multi encounters with them in the past, he knew that their basic powers didn't work on him, so Issei knew he could thoroughly enjoy Ageha without a care.

"Hi! Good evening!" The woman greeted him with a seductive smile as she ran her hand through her blue hair "I believe this is the first time we have met, Lucifer-sama."

"Yes, of course… and Issei is fine, Kurono-san." Issei smiled as he stepped to the side and made a path for her to walk in.

"Then Ageha should be fine." She said, smiling as she turned around to face him "It's an honor to finally meet the famous Lucifer Satan in person." She lowered her body, but Issei could see that she was purposely showing him her cleavage.

"The pleasure is all mine, Ageha-san." Issei took her hand and placed a kiss on the back, smiling at her "You look gorgeous, by the way."

"What a gentleman, Issei-sama! You don't look so bad yourself." She smiled in satisfaction, nodding her head before turning her head around to look at the room he had chosen for them "You have great choice, Issei-sama, even I have never been here before." She said, walking around the room with Issei following behind her.

"I only want the best for my lovely client."

"Just how many women have you taken in here anyway?" She asked playfully and put her bag on the bed before turning around to look at him "No ill intent, of course."

"To tell you the truth, you're the first I brought here." Issei admitted with a smile "It usually happens at my palace or my clients' palaces. I want tonight to be a bit… special."

"Reason?" Ageha asked, leaning closer.

"A lovely lady such as yourself deserves it." He flirted coolly, wrapping his hand around her waist and pulling her closer "You're my client for tonight, Ageha-san, so do not hesitate to ask for anything you want."

"Then don't forget that I'm a succubus, Issei-sama." Ageha licked her lips as she rubbed her soft body against his muscular one before leaning her head slightly so Issei could lower his down and kiss her. Parting his lips, the brown haired Maou moved his tongue into her mouth, and she welcomed it wholeheartedly with hers. His hand went lower, and he could feel her do the same. As he groped her ass, he could feel her hand slide into his pant and go for his dick. Issei could feel her gasping lightly into his mouth when her hand touched the sleeping monster between his legs.

"Now this is what I call a devilish package." Ageha said breathlessly as he broke the kiss and stood there letting her stroke his limp cock with a casual smirk "I must be third luckiest girl of the week." She took her hand back and licked it.

"Only third?" Issei asked.

"The first is your wife, the strongest Queen Grayfia Lucifuge and the second must be Akasha. I guess as your first and second wife, they must have their fills of yours every night." She said and continued with a smile "In case you are wondering, I know Akasha. She's the mother of my daughter's friend at high school. They are chasing after the same guy there."

"Oh, now that you have mentioned it, I believe I must have seen him and the crew when I rescued Akasha from Alucard five years ago." Issei nodded his head thoughtfully while looking up and recalling the battle against Court Dracula. With a smile, he then turned back to her and gestured his hand toward the door "Anyway, why don't we head down to the hotel's restaurant and have dinner? I have booked a table for two for us there."

"Ara, why don't we just start the night already? You know what Succubi eat for meals, right?" She asked seductively, but then said "But of course a man's gotta to eat. It's going to be a long~ night for the both of us, after all." Issei could only nod his head in agreement and put his hand on Ageha's hip, guiding her out of the room before heading down to the restaurant.

Forty five minutes later, the two returned to their room, but as soon as they had gotten out of the elevator, Ageha grabbed him by his collar and pulled his mouth toward hers in a searing kiss. As they furiously made out with each other while groping each other's body, it took Issei sometime to open the door and get them into the room, kicking it close with his foot.

Then suddenly, she pushed him back, making Issei fall into the sofa behind him. Smiling seductive, she reached her hands up and slid her coat down her shoulder, before letting it fall to the floor "Let's get this night started, shall we?" She asked and took a step closer, standing right in front him. Grinning, Issei put his hands on her waists and slowly ran them down to her hips, trailing along her deadly curves "You like?" she asked, lightly swaying her hips around as he pulled his hands up and went under her skirt, squeezing her thighs before stopping at her ass.

"Very." He admitted truthfully. His eyes were focused on her J-cup boobs.

"You're a very honest man, aren't you Issei-sama?" She asked, giggling slightly before saying when she felt his hand wrapping around the waistband of her underwear, a small thong "Pull it down." He did what he was told, and slid it down her thighs, down to her long legs and removed it from her body completely "Can you do the same for this?" Ageha turned around and pulled her hair to the side, showing him the zipper of her dress. Smirking triumphantly, Issei stood up and reached for the zipper before slowly pulling it down, exposing her back and loosing her dress. The zipper stopped just above her supple ass. As she kept the dress from falling off her body with her hands crossing on her breasts, Issei lowered his head down and kissed her neck, holding the succubus by her shoulders. Issei then kissed down to her back, before trailing his lips up to the back of her neck, causing the blue haired woman to moan in response.

Stepping forward, Ageha removed her hands from her chest and let it fall down to her waist, leaving her torso naked. As she moved while swaying her hips, she slowly pushed her dress down, seductively showing him her round ass before dropping it on the floor. Now naked, Ageha continued to move forward until she was by the window, turning around and allowing Issei to take his time drinking in the sight of her voluptuous succubus body, especially her beautiful breasts.

When she made a come over gesture with her finger, without wasting for a second, Issei approached her while removing his shirt. Standing in front of Ageha, Issei reached his hands out and groped her breasts from below, squeezing them in his palms and feeling amazed by the softness. As she leaned her head back, giving him more access, Issei leaned his head forward and captured her left nipple into his mouth, using his tongue to tease the hardening teat, causing Ageha to moan even louder before raising her hands and pushing her tits together for him. Issei accepted the treat with gusto, moving from one to another, while simultaneously molding her tits the way he wanted.

Forcing his head away, Issei stood straight up and kissed Ageha, holding onto her large breasts as he snuggled his tongue into her mouth. The two made out passionately before Ageha moved her hand down and proceeded to remove his pants, getting it down to his thighs and freeing his cock from its confine in only a few seconds. Wrapping her hands around the base of his cock, her fingers couldn't meet around his girth, Ageha started stroking it in rhythm with their heat kiss, her other hands went down to cup his sperm bloated sack, massaging his heavy balls.

Breaking the kiss, Ageha pulled back and waited for him to get himself completely naked to kneel down in front of him, licking her lips as she faced his semi hard cock. Bringing out her tongue, the blue haired succubus teasingly licked the head of his cock, before opening her mouth to take it in, sucking on it lightly before releasing it with a wet kiss.

Holding the impressive man meat with both hands, Ageha traced circles around the head with the flat of her tongue, making Issei grin in approval. Not breaking eye contact, she took three inches of his hard dick into her mouth, slurping lewdly as she moaned in lust at the taste of his delicious cock before releasing him again.

"Now, aren't you such a tease?" Issei asked as he put his hand on the top of her head. The inside of her mouth felt incredible, was the only thing he could describe how good it felt.

"I thought this night was all about me, since I am your client."

"And I still remember that you are a Succubus, Ageha-san." Issei grinned lecherously as he rubbed his cock against her face while she was trying to drench his balls in her spit using her tongue and mouth "Start acting like one, and I might give you a discount next time."

"How can I say no to that?" She said, kissing his cock before taking it into her mouth. When the tip touched the back of her throat, she didn't stop and continued to push forward until she had taken two third of the monster down, making him go cross eye as her gullet clenched tightly around his dick. Sucking like a vacuum, Ageha pulled her head back, nearly extracting his throbbing organ from her gullet, before pushing her head forward, taking nearly his entire cock down her throat, causing Issei to shudder in pleasure. She repeated the process over and over, starting slow but gradually picking up to pace. When her nose finally touched his crotch, Issei nearly lost it and almost blew his load, but kept his composure and stayed strong like that for half an hour long.

Eventually, the building pleasure became too much, and with a groan, Issei blew his first load of the night down her throat after ramming his cock as far down her gullet as he could, overflowing her inside with torrent of thick hot sperm. Issei didn't hold back, and fully enjoyed the pleasure of ejaculating down a succubus' throat. He continued to hose his seeds like that for awhile, forcing Ageha to swallow more cum than she had ever done in her life, before pulling back and letting the head of his cock rest inside her mouth when his orgasm became less intense. Instinctively, she started gulping down his cum once he filled her mouth completely, moaning loudly at the taste. Glancing at the clock, she couldn't believe that he had cum for fifteen minutes straight, and when he was done, his cock was still as hard as steel, urging her to give it another service.

Taking his cock back, Issei watched Ageha as she savored the glob of his sperm with her tongue before swallowing it down in one gulp.

"Delicious." The sultry succubus commented as she wiped the corner of her mouth with the tip of her finger "I have never had such a high quality cum like that before, you are truly blessed with sexual prowess, Issei-sama." She stood up and kissed him before turning around and putting her hands and one foot onto the window frame "I believe I deserve an oral service in return, don't I?" She asked, shaking her as she stuck it out and exposed her dripping pussy.

Issei knew it was his turn to get on his knees, and he did it without hesitation. Kneeling behind her, Issei grabbed her butts, loving how his fingers almost seemed to sink into them. He then moved a hand to her pussy, and inserted two fingers into the hole, causing her to moan in response. As he fingered her pussy at a steady pace, he moved his face forward and licked her ass crack, making her sudden when his tongue gazed her butthole.

Then, without a warning, he drove his head forward and tongued her anus, causing Ageha to gasp in surprise. He continued like that for a few more seconds, before switching his tongue and fingers' positions with each other, licking her pussy while fingering her ass, sending waves of pleasure through her body.

Moving his hands to her butt and holding them with both hands, Issei then drove his tongue into her snatch and started tonguing her inside, lapping the love juice that kept rushing from her core, making Ageha moan loudly in bliss. Succubus' juice was the world's most natural aphrodisiac, so the more he drank it, the hornier he became, but Issei managed to keep his cool and continue pleasuring Ageha for awhile before she came and flooded his mouth with her juice, which he managed to gulp down without spilling a single drop.

"That was so good." Ageha moaned as Issei stood up and wrapped his arms around her body, putting his hands on her boobs, massaging them. Feeling his cock rubbing against her ass, Ageha swayed her hips and shook her ass cheeks, smiling invitingly and seductively "Are you going to fuck me now, Lucifer-sama?"

Grinning, Issei positioned his cock at the entrance of her pussy and plowed straight into her in as soon as he had had a firm grip on her hip, stretching her wide open with a squelch. "Aaaanngh." He moaned in delight while moving his hips at a decent pace "So tight. You have a very nice pussy Ageha-san. It's like you're sucking me in, as expected from a succubus."

"Sweet kami you are big." Ageha threw her head back and wailed in bliss "Oh fuck!" She moaned even louder when Issei increased his pace, her gargantuan booty rippled with every impact of his hips. His thick, impressive cock slid in and out of her swollen, silken, wet tunnel, hitting spots that no man had ever hit in before. Rearing back, Issei then thrust forward and punched right through her cervix and deep into her delightful womb, causing Ageha to go cross-eyed at the impact and cum like she had never cum before. Her tongue lolled out of her mouth and her eyes rolled back, finally loosing herself to the pleasure.

Hooking his arms around her elbows and allowing her breasts to bounce free, Issei kept her close to him like that and started up fucking Ageha's tight twat and womb with short, but fast and powerful thrusts, the sound of his hips smacking her ass and her blissful moan echoed throughout the fancy room. As a succubus, Ageha knew she was supposed to be the one who had more control and made him blow his load first, not the one who came once every two minutes and moaned like she was in heat, but in the end, when she was being fucked like that, there was little that she could do.

Not that she wanted to, since being the one who was at the receiving end like this wasn't so bad.

As Issei got closer to a blissful orgasm, he increased his pace, blurring his hips as and fucking the blue haired succubus as fast as he could. Moments later, he reached his limit and came inside her wholeheartedly, holding nothing back. Ageha had a blissful face and came hard when she felt a massive amount of cum, even larger than the one she had swallowed, started filling her womb as the devil leaned his head back and continued to fuck his load into her while grinning lecherously. Once he was done, he slowly pulled out of his client for the night and watched as a huge deluge of cum started flowing out of her well fucked cunt as she fell to her knees, panting.

"No time to rest, Ageha-san." Issei said as he picked her up and carried her to the bed after she had managed to catch her breath.

"The night is still young, why rush?" Ageha asked teasingly as she was put down to the bed.

"Because I don't want to stop fucking you, that's why." Issei smirked as he got between her legs and spread them with both hands on her knees "It's not like I have succubi to have sex with every day, so get ready Ageha-san, unless you pass out, I am not going to stop fucking you until I am I am thoroughly satisfied."

"Oh… my…" Ageha giggled excitedly and reached her hand down to position his cock at her neither lips "Then please, have it your way then. Fuck me unconscious."

"With pleasure." With that, he thrust his dick in and started savagely hammering his cock into her wet cunt.

There was nothing better than a tight, sensitive succubus who liked to moan.

[ **The next morning** ]

"So, even succubi at her level have their limit." Issei said as he finished putting on his clothes and turned his head around to look at Ageha, who was laying tits down ass up on the bed with a fucked-stupid smile on her face. Her body covered in head to toe in his cum, but he had shot so much of his seeds inside her that she looked nine months pregnant "Well, our contract has expired." Issei said as he lowered his head down and smiled at her "I hope to work with you again, Ageha-san." He kissed her playfully, causing her to whimper in response.

Standing up, Issei made the teleportation magic circle he had left on the floor flash brightly. With a smile, Issei stepped into it and decided whether or not should he return to his place right away. It wasn't a wise thing to do, because Grayfia was probably expecting him to return to get him back to work.

"Maybe I should pay my little sister and her friends a visit." Issei said to himself before nodding his head sagely in agreement with his idea. It'd been awhile since the last time he had met Rias and the others.

Giving Ageha one last look, Issei stepped into the magic circle he had prepared on the floor and teleported straight to the clubroom of the occult research club, where he was greeted by none other than Akeno Himejima, who at the time was sitting on the longue in the middle of the room and doing her homework. Seeing the arrival of him, she immediately dropped what she was doing and stood up so she could greet him with the respect he deserved.

"Issei-sama." She said, bowing "It's my honor to see you here."

"Good morning, Akeno." The brown haired man grinned, raising his hand to signal her to raise her head up "How are you doing?" He stepped out of the magic circle and approached the girl.

"I…" Before she could answer his question, Issei grabbed Akeno around the waist and leaned his body over to kiss her, shoving his tongue into her mouth. She was surprised at first, but quickly melted into the kiss and returned the favor by entangling her tongue with his. After a minute, he released her, allowing the young woman to catch her breath "I am doing fine… thank you, Issei-sama."

"That's good to know." Issei grinned and looked around "Where are Rias and the others?" He asked, before taking a seat on the longue.

"Rias-sama is attending a meeting with the other clubs presidents." The black haired queen answered with a smile "Yuuto-kun and Koneko-chan are having classes, so they won't be able to come here until noon."

"Oh, I see. I guess I will have to wait for Rias then." Issei nodded his head as he ran his hand up and down Akeno's waist.

"Would you like to have some fun with me, Issei-sama?" Akeno said as she snuggled closer to Issei and put her hands on his chest "Surely I can give you something to fill your hands with while waiting for your sister." She asked, and Issei nodded his head in response with a grin. Smiling seductively, Akeno removed the ribbon and let her hair fall freely down her body, before leaning forward to kiss him slow and passionately. His lack of response at first only turned her on even more. After a moment, Issei grinned into her mouth and began to kiss her back, causing Akeno to moan when he slid his tongue into her mouth. As their tongues entangled, Issei could feel her hands pulling down the zipper of his pants and freeing his semi hard cock soon after, her fingers couldn't meet around the impressive girth. She stroked his cock with earnest before taking out his balls and starting to play with them with her other hand.

Breaking the kiss, Issei then spread his legs, signaling Akeno to slide down to the floor. She did it without the need to be told twice, and took it into her mouth, sucking while swirling her tongue around the head before taking it deeper down her throat. It didn't take it long for him to become rock hard in her mouth and when he did, Akeno's hands let go of his cock and went on to remove her shirt before unhooking and doing the same to her bra, allowing her breasts to bounce free.

"You're one hungry slut, aren't you Akeno." Issei said in admiration at how greedily the black haired queen was trying to swallow his cock as if trying to stuff all of it in her stomach. Grabbing her hair to her liking, he pulled her head back and forcefully removed his cock from her mouth "You know, you should hang around my place more often, give you more time with your mother, and me."

"Yes, I would love to, Issei-sama." She purred in response, kissing the tip of his cock before grabbing two handfuls of her enormous breasts and wrapping them around his cock. Smiling seductively, she slid them up and down, pleasuring him with the parts of her body that he loved the most, earning a moan from him in approval.

"Fuck, that's it. You are getting better and better, Akeno." Issei moaned as he released her head from his grip "Keep this up and I might even arrange a night with Grayfia for you." Knowing how much the girl idolized his wife, it could be the best idea ever. Even Issei couldn't stop himself from giggling perversely at the thought of having two busty queens on the same bed.

"Thank you, Issei-sama." After saying that with sparkling eyes, Akeno went back to pleasuring him with her mouth, taking the part that not even her big tits could cover. She moaned passionately around his shaft, before submitting as Issei began to move his hips in sync with her breasts and mouth, holding Akeno by her hair. Since he had already had a lot of sex last night, Issei was able to last really long against Akeno's assault, but eventually his balls tightened and his cock swelled in her mouth. With a loud groan for a warning, Issei flooded Akeno's mouth with a massive helping of hot cum. It took a moment for his orgasm to end, allowing Akeno to slide off his dick "Mmmmm, thank you for the delicious load, my lord." Akeno stated sultrily before placing a wet, slopping kiss on his cock, causing it to throb in response.

"Not bad for me to start a day." Issei said as he leaned his head back and enjoyed the pleasure of Akeno's oral service.

"What do you want to do, Issei-sama?" Akeno purred seductively as she wrapped her hand around his cock and stood up to press her mouth against his. They kissed for a few seconds, before Issei suddenly forced her back with his hand on her neck "Ah, Issei-sama~!" Akeno moaned as he applied some pressure on his grip.

"With a kinky slut like you, Akeno-chan, there are so many things I want to do to you." He said, smirking while teasingly kissing her "But first… I have already told you peaking is very bad, haven't I…Rias-chan?" He suddenly asked loudly and turned his head to the door of the Occult Research Club's clubroom, where its president was kneeling on the floor at the other side, looking at them through the very small gap between the door and the casing.

"Ara ara…." Akeno gasped before starting to giggle uncontrollably (her hands hadn't stopped moving).

"Why don't you come in, Rias-chan?" Issei grinned "There's no point in hiding yourself anymore."

 _Line Break_

When Rias Gremory arrived at her clubroom and saw her queen/best friend sucking her brother off, she wasn't surprised.

In the end, how should feel surprised, when she grew up getting used to seeing him fooling around with women who weren't his wife, Grayfia Lucifuge, and building a harem of beautiful and attractive women out of his peerage. In the society of devils, a Maou wasn't allowed to have a harem, but it didn't take a genius out of Rias for her to see Issei Lucifer had never seemed to be restrained by it.

No, she was annoyed… and jealous.

Why? Because Rias was in love with her brother. She didn't know how, she didn't know when, but for as long as she could remember, she had always had a strong affection for him. Aside from his usual antics, Rias grew up admiring her brother, who loved her dearly and cared for her well-being, even though as a Maou he could never favor a devil over another. That feeling had grown stronger when he managed to convince their parents to cancel her engagement with Raiser Phenex, giving her the opportunity to find happiness.

"But first… I have already told you peaking is very bad, haven't I…Rias-chan?" Rias almost flinched when she heard her brother calling for her "Why don't you come in, Rias-chan?" Without any other choice, Rias pushed open the door of her clubroom and stepped in, doing her best to ignore the sight of his massive cock "Good morning."

"Good morning, Onii-sama." Rias greeted him, doing her best to keep her voice normal "How have you been?"

"As you can see, I am all good." He replied with a grin "What about you, how…"

"Can you…um… put that away first?" Issei looked at his cock when Rias pointed her hand at it and requested nervously.

"Oh…" He said. However, his cock was too hard to be return into his pants, so he went for the next best thing "Akeno-chan, would you like to help me?"

"Of course, Issei-sama." Akeno said knowingly and climbed onto his lap, impaling herself on his cock before using her skirt to cover the rest, earning moans from both of them "There you go, Issei-sama." Grinning, the brown haired Maou gave her a thumb up as Akeno wrapped her arms around his neck and pressed her breasts into his chest.

"Akeno…" Rias muttered in annoyance.

[ **Insert scene here-Waiting to be edited. Y/N: Sorry guys, but I am still trying to figure it out a way to make the conversation between Issei and Rias as good as possible. Since I cannot delay the update any longer, I have decided to leave it like this and add new part when I update new chapter. Please forgive me for this, but I don't think I have any other choice.** ]

 _Line Break_

Issei wasted no time after he had finished with Akeno, who was left with a pregnant-like belly, and took the two of them to Rias' apartment via teleportation magic circle.

The moment he had been waiting for had finally arrived, and he knew he was going to enjoy every second of it.

"Are we…" Without giving her the chance to finish her question, Issei turned Rias around and kissed her, catching the young lady by surprise. Rias was a little hesitate, at first, but quickly steeled her nerves and kissed him back, submitting to the kiss and closing her eyes and letting her brother explore her mouth, which unknown to her wasn't the first time. The two moaned as their kissing started to heat up, one of Issei's hands soon found its way up her body and ultimately filled itself with her right breast, while the other trailed down to her ass and did the same to her supple butt through the silky fabric of the panties she was wearing.

Rias gave no objection. She was new. She was inexperienced. Everything she knew about sex was through movies, porn, and also her secret collection of hentai anime. She wanted to make the best of it, but she didn't want to mess up, so she allowed Issei, who had so much experience already, to take the lead. While still kissing her, Issei unbuttoned her shirt, and removed it from her body. He quickly did the same to her lacy bra, and freed her breasts from its binding. Next, he broke the kiss and latched on them like a hungry animal. Using both hands, he kneaded and played groped her breasts the ways he wanted, his sucking mouth sealed firmly around her nipple, and only broke away when he decided to move onto the other, earning moans and gasps from Rias in response. Rias could only stand there and let him enjoy her body, so aggressive that he pushed her toward the bed and made her fall on her back, with him on top.

"You really love breasts, don't you onii-sama?" Rias asked, arching her back in pleasure.

"Yes, and I like them best when they are big, soft and bouncy." Issei replied as he broke his face away from her chest and shot his head forward to kiss her "Yours are simply the best."

"I bet you said that to every woman you brought to your bedroom." That was not a question, making Issei respond with a chuckle "Pervert…" She stated with a pout, but before she could say anything else, Issei sealed her lips tight and shoved his tongue into her mouth, preventing her from uttering another word. As Rias once again struggled to keep up with her brother, Issei used his magic to remove his clothes, allowing his semi-hard dick to spring free and leaving him completely naked on top of his sister.

"I am." Pulling back, Issei told her with a sly smirk before standing up and straddling her torso. Her eyes followed his movement, and immediately glued to his cock when it had finally come into her sight "Now, the moment of truth." He declared happily. This was it. This was the moment he had been waiting for, and without waiting for another second, he grabbed her tits and smashed them together with his cock in between, moaning at the amazing softness around his cock "Fuck…" He whispered in amazement and moved his hips just a few times for a quick test. The feeling was beyond what he had imagined.

Rias looked at the pleasure expression on his face and, for some unknown reason, couldn't help but feel proud of herself. As he moved his hips, allowing his cock to slide between her tits soft embrace, she could feel the engorged head of his cock rubbing against her lips and nearly poking against her nose, smearing a fair amount of hot pre-cum around that part of her face. She opened her mouth, and licked her upper lips, having a taste of his cum on the tip and then all over of her tongue. It tasted nothing like she had imagined, but Rias believed she had finally known why his maids, even Grayfia, loved spending their times under his table.

"A much bigger treat is waiting for you." Issei said as he stopped his hips and started moving her breasts up and down his steel hard dick "Suck my cock, Rias." He told her with a hint of authority in his tone, and Rias could only nod her head in response. He was her brother, but incest was just a word in the society of devils, and who was she to defy a wish of a Maou?

Opening her mouth, Rias took in the bulbous head of his cock, and found herself slurping on it a second later, her tongue madly licking his slit and around the glans of his cock. Issei leaned his head back, and pushed his hips forward slightly, cramping more of his cock into her mouth. Rias gave no objection, and continued to suck and lick the part of his cock that was inside her mouth. She didn't know how to do it probably, so he had hit her teeth a couple of times, but Issei didn't mind. Back in the old world, he had imagined Rias would be like this during their first time: eager but sloppy (which could be said the same for his). She might be a she-devil who had acted seductive and worn skimpy lingerie around him, but in the end, she was just another innocent teenager to love, and anything that would involve if they had decided to take the next step.

He was a pussy and a fool back then, he had to admit. The other girls were a different story, but Rias and Akeno had made several attempts to sleep with him, and he had refused them because he thought he didn't feel like he had earned the right to do so. Two young and beautiful women would do anything to please him, and yet he had decided to spend the majority of his time feeling his youth, aka jacking off to their naked images and the fantasies of having sex with them in his head. Sure, that bitch Raynare, who he was eager to meet as soon as she decided to make a move at Kuoh for whatever reason it was going to, had a hand in his feelings, but he wouldn't deny the fact that he had been very pathetic back then. Ophis and Great Red resetting the world simply gave him a means to maintain peace, and what it takes to archive his own happiness.

Looking at the woman who was having her breasts embraced his cock, and sucking on one third of the same thing, he couldn't help but feel amazed at the feelings she had for him. (As it had been said before, the two dragon gods had made sure to keep the feelings of the girls he cared about at unconscious-level). Her love was so great she didn't have a single problem admitting her love for him even though in this world he was her biological brother. Sure, there was no such thing as incest when you were a devil, but logically that had always been a questionable subject whenever you were a living being.

Thick meaty slaps filled the room as Issei started fucking her tits for real, drastically moving his hips back and forth with his cock secured in a tight grip of her tits.

"Fuck Rias-chan! Here I come!"

Issei felt his balls tighten and Rias could feel his cock swelled even bigger inside of her mouth. She braced herself for it, but she didn't expect him to release her breasts and shoot forward to grab her by the back of her head to raise her head up before pushing his cock deep in her throat to come. Rias did her best to swallow, but she couldn't even swallow half of load before the next followed, causing his cum to spill out from the corners of her outstretched mouth, making a mess on her cheeks and the lower half of her face.

After a moment, Issei pulled his cock out with a wet pop and kept her head where it was, jerking his cock a few more times before painting the rest of her face white in his cum. After he was done cumming, Issei allowed Rias to suck for the last helpings of cum before sitting down at the sight, sighing stupidly in satisfaction.

"Man… that was…" But before he could say that, Rias sat up and shot her hand out to pinch his cheek, glaring at him with a cute pout "Ouch… Ria…han…It…hurt…" Actually, it didn't hurt that much, since it was nowhere near Grayfia's level, but he still had trouble talking with his cheek being pinched like that.

"What was that at the end?" Rias asked with half lifted eyes and an evil smile "Did you want me to drown in your cum or get suffocated to death?" Her other hand went down and took hold of his balls, massaging them a little harder than his liking.

"I… don't see the problem." He grinned when Rias released her hold on his cheek "Don't tell me that you don't like it, Rias-chan." Saying that, Issei moved his hands under her skirt and grabbed the waistband of her panties, tearing it apart before pushing her down to the bed with his whole body. Lying on top of her, Issei rubbed her outer lips, feeling how wet it was before inserting his middle finger into her pussy.

"Tight and wet, just the way I like it." The brown haired devil commented as he felt her wall squeezed tightly around his finger.

"Then what are you waiting for…" Rias said between moans "Put it in already."

"Impatient, aren't we?" He smirked "Well then…" Removing is hand from her fold, Issei took hold of her thighs and spread her legs apart, allowing him to position himself underneath her. Rias hips raised and aligned to receive his cock wholeheartedly "Let me warn you though… it's going to hurt a lot. Are you ready?"

"Yes." Rias nodded nervously. Without further ado, Issei thrust his hip forward and buried four inches of his cock into her pussy, breaking through her hymen rather viciously and causing Rias to groan in pain. Despite the wonderful feeling of her pussy, Issei didn't move and allowed the pain to ease down and Rias to get used to the monstrous size of his cock.

Still, like any she-devil he had fucked, it didn't take it long for the pain of having her hymen broken to disappear completely. When painful groan became moan of pleasure, Issei started to move his hips, nearly pulling his cock out before thrusting forward, adding two more inches. Rias' pussy was tight, there was no doubt about that, but she was wet enough for him to move in and out of her easily.

"C-can you move faster?" Rias asked, putting her hands on his shoulders to brace herself.

"As you wish." Grinning, Issei fulfilled her wish, moving his hip a little faster and gradually building up speed. Bending his body forward, Issei used one hand to grab and tease her breast, while the other one was still holding onto her left leg. Rias' right leg immediately shot up and wrapped itself around his waist as his thrusting became wilder and his cock got deeper into her.

"Ah… ah…" Rias moaned out loud as the cock of her brother finally reached the deepest parts of her pussy and hit against the entrance to her womb with each thrust. The feeling of having her inside violated by his cock was simply amazing.

"Fuck..." Issei moaned as he focused on moving his hips while his hand seemingly sink into her incredibly soft and large bust as he grabbed it roughly. Her back arched as Issei started to have his way with her at his normal speed and strength, drowning her in the pleasure. The young crimson haired woman couldn't even form actual words as she started come harder and faster than she ever had from fingering herself or 'playing' with her queen while fantasying about her brother "This feels so good!" Issei yelled as he threw his head back and turned his hips into a blur, punching through her cervix and got plenty of his cock into her womb, causing Rias to cry and cum harder than she had ever done before.

It took a good forty or more minutes before he finally felt his balls clenching and his cock throbbing uncontrollably inside Rias' pussy and womb. With one final thrust as far into her as he could, Issei let loose a powerful dose of hot and thick cum into her womb, filling it to the brim. He stayed like that for over eight or so minutes, before pulling out while still coming and spray several ropes onto her face and breasts, once again painting them white.

"You're mine now, Rias-chan." Issei grinned as he continued to stroke his cock and pour his cum onto Rias' body, which was still twitching and jerking every now and then due to the aftermath of her mind-blowing orgasms "Ready for the second round?" Issei grinned, cock twitching.

Rias could only whimper in response as Issei picked her up.

* * *

 **End of Chapter 6**

* * *

 **Here you go… sorry for taking this long to update. It took me awhile to get this chapter done, especially when my computer broke a few days ago and I was kind of busy with the more serious stories.**

 **Anyway, here it is folks, I hope you have enjoyed this chapter.**

 **Ageha Kurono is from Rosario Vampire. Since Akasha has already been added, why not bringing in other characters as well?**

 **Well, that's it for now.**

 **READ and REVIEW!**

 **Ja ne!**

 **P/S: Would you like it if I take this story to a more serious direction?**


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